2-amino-1,3-propanediol compound and immunosuppressant

ABSTRACT

A 2-amino-1,3-propanediol compound represented by general formula (I) or a pharmaceutically acceptable salt thereof, and an immunosuppressant containing the same as the active ingredient. In said formula R represents optionally substituted linear or branched carbon chain, optionally substituted aryl or optionally substituted cycloalkyl; and R 2 , R 3 , R 4  and R 5 , which may be the same or different from one another, represent each hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl. The compound is immunodepressant and useful as an inhibitor against rejection in organ or bone marrow transplantation, as a preventive or remedy for autoimmune diseases and so forth, or a reagent in the medical and pharmaceutical fields. ##STR1##

This is a divisional application of Ser. No. 08/244,942, filed asPCT/JP93/01515, Oct. 18, 1993, now U.S. Pat. No. 5,604,227.

TECHNICAL FIELD

The present invention relates to 2-amino-1,3-propanediol compoundsuseful as pharmaceuticals, particularly as an immunosuppressant.

BACKGROUND ART

In recent years, cyclosporin is in use for suppressing rejectiondeveloped in transplanting organs. Inclusive of the compounds currentlyunder development, the so-called immunosuppressants are expected to beuseful as therapeutic agents for articular rheumatism and so on. Saidcyclosporin, however, also poses problems of side effects such as renaldisorders.

Meanwhile, Japanese Patent Unexamined Publication No. 104087/1989discloses that an immunosuppressive substance is obtained from a liquidculture of Isaria sinclairii and said substance has been confirmed to be(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-hydroxymethyl-14-oxoicosa-6-enoicacid of the formula ##STR2## disclosed in U.S. Pat. No. 3928572. Inaddition, Japanese Patent Unexamined Publication No. 128347/1991 statesthat a series of said compound has an immunosuppressive action.

Referring to Merck Index, 11th edition, it is described that2-amino-2-methyl-1,3-propanediol (Index No. 460),2-amino-2-ethyl-1,3-propanediol (Index No. 451) and2-amino-2-hydroxymethyl-1,3-propanediol (also called tromethamine, IndexNo. 9684) can be used as surfactants, intermediates for pharmaceuticals,emulsifiers or gas adsorbents and that tromethamine is medically usableas an alkalization agent. In Japanese Patent Unexamined Publication No.416/1987, a hair dye containing 2-amino-2-(C1-C5 alkyl)-1,3-propanediolis disclosed. U.S. Pat. No. 4,910,218 and J. Med. Chem., vol. 33,2385-2393 (1990) teach 2-amino-2-(methyl or ethyl)-1,3-propanediol as anintermediate for an antitumor agent. Also, Japanese Patent UnexaminedPublication No. 192962/1984 teaches that the aforementioned2-amino-2-(C1-C5 alkyl)-1,3-propanediol or 2-amino-1,3-propanediol canbe used as a stabilizer for an antigen or antibody-sensitized latexreagent. Moreover, U.S. Pat. No. 3,062,839 teaches 2-methyl- orethyl-amino-2-(furylmethyl, phenylmethyl or phenylmethyl substituted bylower alkyl, lower alkoxy, chloro, hydroxy or unsubstitutedamine)-1,3-propanediol having a tranquilizer action and J. Org. Chem.,vol. 25, 2057-2059 (1960) teaches 2-methylamino-2-(phenylmethyl orphenylmethyl substituted by 2-methyl, 3-methyl, 4-methyl, 4-methoxy or4-hydroxy)-1,3-propanediol. It is not known, however, that thesecompounds have immunosuppressive actions such as suppression ofrejection developed in organ transplantation, prevention and treatmentof autoimmune diseases and the like.

An object of the present invention is to provide novel2-amino-1,3-propanediol compounds having superior immunosuppressiveaction with less side effects.

DISCLOSURE OF THE INVENTION

The present invention relates to

(1) a 2-amino-1,3-propanediol compound of the formula ##STR3## wherein Ris an optionally substituted straight- or branched carbon chain whichmay have, in the chain, a bond, a hetero atom or a group selected fromthe group consisting of a double bond, a triple bond, oxygen, sulfur,sulfinyl, sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acylor alkoxycarbonyl, carbonyl, optionally substituted arylene, optionallysubstituted cycloalkylene, optionally substituted heteroarylene and analicycle thereof, and which may be substituted, at the chain endthereof, by a double bond, a triple bond, optionally substituted aryl,optionally substituted cycloalkyl, optionally substituted heteroaryl oran alicycle thereof; an optionally substituted aryl, an optionallysubstituted cycloalkyl, an optionally substituted heteroaryl or analicycle thereof; and

R², R³, R⁴ and R⁵ are the same or different and each is a hydrogen, analkyl, an aralkyl, an acyl, or an alkoxycarbonyl, or R⁴ and R⁵ may bebonded to form an alkylene chain which may be substituted by alkyl, arylor aralkyl;

wherein the optionally substituted straight- or branched carbon chainmay have a substituent selected from the group consisting of alkoxy,alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino,hydroxyimino, hydroxy, carboxy, optionally substituted aryl, optionallysubstituted aryloxy, optionally substituted cycloalkyl, optionallysubstituted heteroaryl and an alicycle thereof; the aforementionedoptionally substituted arylene, optionally substituted cycloalkylene,optionally substituted heteroarylene and an alicycle thereof may have asubstituent selected from the group consisting of alkoxy, alkenyloxy,alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio,acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl,haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxy and carboxy; andthe optionally substituted aryl, optionally substituted aryloxy,optionally substituted cycloalkyl, optionally substituted heteroaryl andan alicycle thereof may have a substituent selected from the groupconsisting of alkyl, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, haloalkoxy,nitro, halogen, amino, hydroxy and carboxy;

provided that when R is C1-C5 alkyl, the alkyl should be substituted andwhen R is furylmethyl, phenylmethyl or phenylmethyl substituted by loweralkyl, lower alkoxy, chloro, hydroxy or amino, one of R² and R³ is notmethyl or ethyl, and a pharmaceutically acceptable salt thereof;

(2) a 2-amino-1,3-propanediol compound according to the above-mentioned(1), having the formula ##STR4## wherein R¹ is an optionally substitutedstraight- or branched carbon chain which may have, in the chain, a bond,a hetero atom or a group selected from the group consisting of a doublebond, a triple bond, oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- whereR⁶ is hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl, carbonyl,optionally substituted arylene, optionally substituted cycloalkylene,optionally substituted heteroarylene and an alicycle thereof; and whichmay be substituted, at the chain end (ω-position) thereof, by a doublebond, a triple bond, optionally substituted aryl, optionally substitutedcycloalkyl, optionally substituted heteroaryl or an alicycle thereof; anoptionally substituted aryl, an optionally substituted cycloalkyl, anoptionally substituted heteroaryl or an alicycle thereof; and

R², R³, R⁴ and R⁵ are the same or different and each is a hydrogen, analkyl, an aralkyl, an acyl or an alkoxycarbonyl, or R⁴ and R⁵ may bebonded to form an alkylene chain which may be substituted by alkyl, arylor aralkyl;

wherein the optionally substituted straight- or branched carbon chainmay have a substituent selected from the group consisting of alkoxy,alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino,hydroxyimino, hydroxy, carboxy, optionally substituted aryl, optionallysubstituted aryloxy, optionally substituted cycloalkyl, optionallysubstituted heteroaryl and an alicycle thereof; and the aforementionedoptionally substituted arylene, optionally substituted cycloalkylene,optionally substituted heteroarylene, an alicycle thereof, optionallysubstituted aryl, optionally substituted aryloxy, optionally substitutedcycloalkyl, optionally substituted heteroaryl and an alicycle thereofmay have a substituent selected from the group consisting of alkoxy,alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxyand carboxy;

provided that when R¹ is C1-C4 alkyl, the alkyl should be substitutedand when R¹ is furyl, phenyl or phenyl substituted by lower alkyl, loweralkoxy, chloro, hydroxy or amino, one of R² and R³ is not methyl orethyl, and a pharmaceutically acceptable salt thereof;

(3) a 2-amino-1,3-propanediol compound according to the above-mentioned(1) or (2), having the formula ##STR5## wherein R¹ a is an optionallysubstituted straight- or branched carbon chain which may have, in thechain, a bond, a hetero atom or a group selected from the groupconsisting of a double bond, a triple bond, oxygen, sulfur, sulfinyl,sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acyl oralkoxycarbonyl, carbonyl, optionally substituted phenylene andoptionally substituted cycloalkylene; an optionally substituted phenylor an optionally substituted cycloalkyl; and

R² a, R³ a, R⁴ a and R⁵ a are the same or different and each is ahydrogen, an alkyl, an acyl or an alkoxycarbonyl; wherein the optionallysubstituted phenyl and optionally substituted cycloalkyl may have asubstituent selected from the group consisting of optionally substitutedstraight- or branched carbon chain which may have, in the chain, a bond,a hereto atom or a group selected from the group consisting of a doublebond, a triple bond, oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- whereR⁶ is hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl, carbonyl,optionally substituted phenylene and optionally substitutedcycloalkylene; alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, nitro, halogen,amino, hydroxy, carboxy, optionally substituted phenyl, optionallysubstituted phenoxy and optionally substituted cycloalkyl; theoptionally substituted carbon chain may have a substituent selected fromthe group consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, nitro, halogen,amino, hydroxy, carboxy, optionally substituted phenyl, optionallysubstituted phenoxy and optionally substituted cycloalkyl; and theaforementioned optionally substituted phenylene, optionally substitutedcycloalkylene, optionally substituted phenyl, optionally substitutedphenoxy and optionally substituted cycloalkyl may have a substituentselected from the group consisting of alkoxy, alkenyloxy, alkynyloxy,aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio, acylamino,alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl,nitro, halogen, amino, hydroxy and carboxy; provided that when R¹ a isC1-C4 alkyl, the alkyl should be substituted and when R¹ a is furyl,phenyl or phenyl substituted by lower alkyl, lower alkoxy, chloro,hydroxy or amino, one of R² a and R³ a is not methyl or ethyl, and apharmaceutically acceptable salt thereof;

(4) a 2-amino-1,3-propanediol compound according to the above-mentioned(3), having the formula ##STR6## wherein R¹ b is an optionallysubstituted alkyl, an optionally substituted alkenyl, an optionallysubstituted alkynyl, an optionally substituted phenyl or an optionallysubstituted cycloalkyl, and

R² b, R³ b, R⁴ b and R⁵ b are the same or different and each is ahydrogen, an alkyl or an acyl;

wherein the optionally substituted alkyl, optionally substituted alkenyland optionally substituted alkynyl may have a substituent selected fromthe group consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, nitro, halogen, amino,hydroxy, carboxy, optionally substituted phenyl and optionallysubstituted cycloalkyl; and the aforementioned optionally substitutedphenyl and optionally substituted cycloalkyl may have 1 to 3substituents selected from the group consisting of alkyl, alkenyl,alkynyl, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, nitro, halogen, amino, hydroxy and carboxy;

provided that when R¹ b is C1-C4 alkyl, the alkyl should be substitutedand when R¹ b is furyl, phenyl or phenyl substituted by lower alkyl,lower alkoxy, chloro, hydroxy or amino, one of R² b and R³ b is notmethyl or ethyl, and a pharmaceutically acceptable salt thereof;

(5) a 2-amino-1,3-propanediol compound according to the above-mentioned(1), (2), (3) or (4), having the formula ##STR7## wherein Ra is astraight- or branched chain alkyl having 12 to 22 carbon atoms, whichmay have, in the chain, a bond or a hetero atom selected from the groupconsisting of a double bond, a triple bond, oxygen, sulfur, sulfinyl,sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acyl oralkoxycarbonyl, and carbonyl, and which may have, as a substituent,alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, acyl, alkylamino, alkylthio,acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl,nitro, halogen, amino, hydroxyimino, hydroxy or carboxy, and

R² b, R³ b, R⁴ b and R⁵ b are the same or different and each is ahydrogen, an alkyl or an acyl, and a pharmaceutically acceptable saltthereof;

(6) a 2-amino-1,3-propanediol compound according to the above-mentioned(5), having the formula ##STR8## wherein Rb is a straight- or branchedchain alkyl having 13 to 20 carbon atoms, which may have, in the chain,an oxygen atom and which may have, as a substituent, nitro, halogen,amino, hydroxy or carboxy, and

R² c and R³ c are the same or different and each is a hydrogen or analkyl, and a pharmaceutically acceptable salt thereof;

(7) a 2-amino-1,3-propanediol compound according to the above-mentioned(5) or (6), having the formula ##STR9## wherein Rc is a straight- orbranched chain alkyl having 13 to 20 carbon atoms or a straight- orbranched chain alkyl having 13 to 20 carbon atoms which is substitutedby halogen, and a pharmaceutically acceptable salt thereof;

(8) a 2-amino-1,3-propanediol compound according to the above-mentioned(5), (6) or (7), which is selected from2-amino-2-tridecyl-1,3-propanediol,2-amino-2-tetradecyl-1,3-propanediol,2-amino-2-pentadecyl-1,3-propanediol,2-amino-2-hexadecyl-1,3-propanediol,2-amino-2-heptadecyl-1,3-propanediol,2-amino-2-octadecyl-1,3-propanediol,2-amino-2-nonadecyl-1,3-propanediol, 2-amino-2-icosyl-1,3-propanediol,2-amino-2-(12-fluorododecyl)-1,3-propanediol and2-amino-2-(14-fluorotetradecyl)-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(9) a 2-amino-1,3-propanediol compound according to the above-mentioned(1), (2), (3) or (4), having the formula ##STR10## wherein Rd is aphenylalkyl, a substituted phenylalkyl, a cycloalkylalkyl, a substitutedcycloalkylalkyl, a heteroarylalkyl, a substituted heteroarylalkyl, aheterocyclic alkyl or a substituted heterocyclic alkyl,

wherein the alkyl moiety may have, in the carbon chain, a bond or ahetero atom selected from the group consisting of a double bond, atriple bond, oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- where R⁶ ishydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl, and carbonyl, and mayhave, as a substituent, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, nitro, halogen, amino,hydroxy or carboxy; and the substituted phenylalkyl, substitutedcycloalkylalkyl, substituted heteroarylalkyl and substitutedheterocyclic alkyl may have a substituent selected from the groupconsisting of alkyl, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,haloaralkyloxy, aralkyloxyalkyl, phenoxyalkyl, phenoxyalkoxy,alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, haloalkoxy,nitro, halogen, amino, hydroxy and carboxy, and a pharmaceuticallyacceptable salt thereof;

(10) a 2-amino-1,3-propanediol compound according to the above-mentioned(9), having the formula ##STR11## wherein Re is a phenylalkyl whereinthe alkyl moiety is a straight- or branched chain having 6 to 20 carbonatoms; a phenylalkyl which may be substituted by a straight- or branchedchain C6-C20 alkyl optionally substituted by halogen, a straight- orbranched chain C6-C20 alkoxy optionally substituted by halogen, astraight- or branched chain C6-C20 alkenyloxy, phenylalkoxy,halophenylalkoxy, phenylalkoxyalkyl, phenoxyalkoxy or phenoxyalkyl; acycloalkylalkyl wherein the alkyl moiety is a straight- or branchedchain having 6 to 20 carbon atoms; a cycloalkylalkyl substituted by astraight- or branched chain alkyl having 6 to 20 carbon atoms; aheteroarylalkyl wherein the alkyl moiety is a straight- or branchedchain having 6 to 20 carbon atoms; a heteroarylalkyl substituted by astraight- or branched chain alkyl having 6 to 20 carbon atoms; aheterocyclic alkyl wherein the alkyl moiety is a straight- or branchedchain having 6 to 20 carbon atoms, or a heterocyclic alkyl substitutedby a straight- or branched chain alkyl having 6 to 20 carbon atoms;

wherein the alkyl moiety may have, in the carbon chain, a bond or ahereto atom selected from the group consisting of a double bond, atriple bond, oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- where R⁶ ishydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl, and carbonyl, and mayhave, as a substituent, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, nitro, halogen, amino,hydroxy or carboxy, and a pharmaceutically acceptable salt thereof;

(11) a 2-amino-1,3-propanediol compound according to the above-mentioned(9) or (10), having the formula ##STR12## wherein Rf is a phenylalkylwherein the alkyl moiety is a straight- or branched chain having 6 to 20carbon atoms which may have, in the carbon chain, one or two oxygenatoms; a phenylalkyl which may be substituted by a straight- or branchedchain C6-C20 alkyl optionally substituted by halogen, a straight- orbranched chain C6-C20 alkoxy optionally substituted by halogen, astraight- or branched chain C6-C20 alkenyloxy, phenylalkoxy,halophenylalkoxy, phenylalkoxyalkyl, phenoxyalkoxy or phenoxyalkyl; acycloalkylalkyl wherein the alkyl moiety is a straight- or branchedchain having 6 to 20 carbon atoms which may have, in the carbon chain,one or two oxygen atoms; a cycloalkylalkyl substituted by a straight- orbranched chain alkyl having 6 to 20 carbon atoms; a heteroarylalkylwherein the alkyl moiety is a straight- or branched chain having 6 to 20carbon atoms which may have, in the carbon chain, one or two oxygenatoms; a heteroarylalkyl substituted by a straight- or branched chainalkyl having 6 to 20 carbon atoms; a heterocyclic alkyl wherein thealkyl moiety is a straight- or branched chain having 6 to 20 carbonatoms which may have, in the carbon chain, one or two oxygen atoms, or aheterocyclic alkyl substituted by a straight- or branched chain alkylhaving 6 to 20 carbon atoms;

wherein the alkyl moiety may have, in the carbon chain, a substituentselected from the group consisting of alkoxy, alkenyloxy, alkynyloxy,aralkyloxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, nitro, halogen, amino,hydroxy and carboxy, and a pharmaceutically acceptable salt thereof;

(12) a 2-amino-1,3-propanediol compound according to the above-mentioned(9), (10) or (11), having the formula ##STR13## wherein Rg is aphenylalkyl wherein the alkyl moiety is a straight- or branched chainhaving 6 to 20 carbon atoms which may have, in the carbon chain, one ortwo oxygen atoms, a phenylalkyl which may be substituted by a straight-or branched chain C6-C14 alkyl optionally substituted by halogen, astraight- or branched chain C6-C14 alkoxy optionally substituted byhalogen, a straight- or branched chain C6-C14 alkenyloxy, phenylalkoxy,halophenylalkoxy, phenylalkoxyalkyl, phenoxyalkoxy or phenoxyalkyl; acycloalkylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms; acycloalkylalkyl substituted by a straight- or branched chain alkylhaving 6 to 14 carbon atoms; a heteroarylalkyl wherein the alkyl moietyhas 6 to 20 carbon atoms; a heteroarylalkyl substituted by a straight-or branched chain alkyl having 6 to 14 carbon atoms; a heterocyclicalkyl wherein the alkyl moiety has 6 to 20 carbon atoms, or aheterocyclic alkyl substituted by a straight- or branched chain alkylhaving 6 to 14 carbon atoms, and a pharmaceutically acceptable saltthereof;

(13) a 2-amino-1,3-propanediol compound according to the above-mentioned(12), having the formula ##STR14## wherein Rh is a phenylalkyl whereinthe alkyl moiety has 6 to 20 carbon atoms, a phenylalkoxyalkyl whereinthe alkyl moiety and alkoxy moiety have 6 to 20 carbon atoms in total, aphenoxyalkyl wherein the alkyl moiety has 6 to 20 carbon atoms or aphenoxyalkoxyalkyl wherein the alkyl moiety and alkoxy moiety have 6 to20 carbon atoms in total, and a pharmaceutically acceptable saltthereof;

(14) a 2-amino-1,3-propanediol compound according to the above-mentioned(13), which is selected from the group consisting of2-amino-2-(8-phenyloctyl)-1,3-propanediol,2-amino-2-(9-phenylnonyl)-1,3-propanediol,2-amino-2-(10-phenyldecyl)-1,3-propanediol,2-amino-2-(11-phenylundecyl)-1,3-propanediol,2-amino-2-(12-phenyldodecyl)-1,3-propanediol,2-amino-2-(13-phenyltridecyl)-1,3-propanediol,2-amino-2-(14-phenyltetradecyl)-1,3-propanediol,2-amino-2-(15-phenylpentadecyl)-1,3-propanediol,2-amino-2-(16-phenylhexadecyl)-1,3-propanediol, 2-amino-2-6-(8-phenyloctyloxy)hexyl!-1,3-propanediol,2-amino-2-(8-phenylmethyloxyoctyl)-1,3-propanediol,2-amino-2-(9-phenoxynonyl)-1,3-propanediol,2-amino-2-(12-phenoxydodecyl)-1,3-propanediol and 2-amino-2-6-(2-phenoxyethyloxy)hexyl!-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(15) a 2-amino-1,3-propanediol compound according to the above-mentioned(13) which is selected from the group consisting of2-amino-2-(10-phenyldecyl)-1,3-propanediol,2-amino-2-(13-phenyltridecyl)-1,3-propanediol, 2-amino-2-6-(8-phenyloctyloxy)hexyl!-1,3-propanediol,2-amino-2-(8-phenylmethyloxyoctyl)-1,3-propanediol,2-amino-2-(9-phenoxynonyl)-1,3-prepanediol,2-amino-2-(12-phenoxydodecyl)-1,3-propanediol and 2-amino-2-6-(2-phenoxyethyloxy)hexyl!-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(16) a 2-amino-1,3-propanediol compound according to the above-mentioned(12), having the formula ##STR15## wherein Ri is a phenylalkylsubstituted by a straight- or branched chain C6-C14 alkyl optionallysubstituted by halogen, a straight- or branched chain C6-C14 alkoxyoptionally substituted by halogen or a straight- or branched chainC6-C14 alkenyloxy;

wherein the alkyl moiety of phenylalkyl maybe substituted by hydroxy,and a pharmaceutically acceptable salt thereof;

(17) a 2-amino-1,3-propanediol compound according to the above-mentioned(16), having the formula ##STR16## wherein Rj is a phenylalkylsubstituted by a straight- or branched chain C6-C14 alkyl optionallysubstituted by halogen, a straight- or branched chain C6-C14 alkoxyoptionally substituted by halogen or a straight- or branched chainC6-C14 alkenyloxy, wherein the alkyl moiety is a C2-C6 alkyl optionallysubstituted by hydroxy, and a pharmaceutically acceptable salt thereof;

(18) a 2-amino-1,3-propanediol compound according to the above-mentioned(16) or (17), which is selected from the group consisting of 2-amino-2-2-(4-heptylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-octylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-nonylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-decylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-undecylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-dodecylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-tridecylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-tetradecylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-hexyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-heptyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-octyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-nonyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-decyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-undecyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-dodecyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-tridecyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(8-fluorooctyl)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(12-fluorododecyl)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(7-fluoroheptyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2- 2-2-(4-(11-fluoroundecyloxy)phenyl)ethyl!-1,3-propanediol and 2-amino-2-2-(4-(7-octenyloxy)phenyl)ethyl!-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(19) a 2-amino-1,3-propanediol compound according to the above-mentioned(16) or (17), which is selected from the group consisting of 2-amino-2-2-(4-heptylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-octylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-nonylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-decylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-undecylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-dodecylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-heptyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-octyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-nonyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-undecyloxyphenyl)ethyl!-1,3-propanediol and 2-amino-2-2-(4-(7-octenyloxy)phenyl)ethyl!-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(20) a 2-amino-1,3-propanediol compound according to the above-mentioned(12), having the formula ##STR17## wherein Rk is a phenylalkylsubstituted by phenylalkoxy, halophenylalkoxy, phenylalkoxyalkyl,phenoxyalkoxy or phenoxyalkyl, and a pharmaceutically acceptable saltthereof;

(21) a 2-amino-1,3-propanediol compound according to the above-mentioned(20), having the formula ##STR18## wherein R¹ is a phenylalkylsubstituted by phenylalkoxy wherein the alkoxy moiety has 2 to 8 carbonatoms, halophenylalkoxy wherein the alkoxy moiety has 2 to 8 carbonatoms, phenylalkoxyalkyl wherein the alkoxy moiety and alkyl moiety have2 to 8 carbon atoms in total, phenoxyalkoxy wherein the alkoxy moietyhas 2 to 8 carbon atoms or phenoxyalkyl wherein the alkyl moiety has 2to 8 carbon atoms, where the alkyl moiety has 2 to 6 carbon atoms, and apharmaceutically acceptable salt thereof;

(22) a 2-amino-1,3-propanediol compound according to the above-mentioned(20) or (21), which is selected from the group consisting of 2-amino-2-2-(4-phenylmethyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(2-phenylethyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(3-phenylpropyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(4-phenylbutyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(5-phenylpentyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(14-(6-phenylhexyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(7-phenylheptyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(8-phenyloctyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-4-(6-(4-fluorophenyl)hexyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(5-phenylpentyloxymethyl)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(4-phenoxybutyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(5-phenoxypentyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(6-phenoxyhexyloxy)phenyl)ethyl!-1,3-propanedio, 2-amino-2-2-(4-(7-phenoxyheptyloxy)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(4-phenoxybutyl)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(5-phenoxypentyl)phenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(6-phenoxyhexyl)phenyl)ethyl!-1,3-propanediol and 2-amino-2-2-(4-(7-phenoxyheptyl)phenyl)ethyl!-1,3-propanediol, and apharmaceutically acceptable salt thereof;

(23) a 2-amino-1,3-propanediol compound according to the above-mentioned(20) or (21) which is selected from the group consisting of 2-amino-2-2-(4-(6-phenylhexyloxy)phenyl)ethyl!-1,3-propanediol and 2-amino-2-2-(4-(5-phenylpentyloxymethyl)phenyl)ethyl!-1,3-propanediol, and apharmaceutically acceptable salt thereof;

(24) a 2-amino-1,3-propanediol compound according to the above-mentioned(12), having the formula ##STR19## wherein Rm is an alkyl-substitutedcycloalkylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms intotal, and a pharmaceutically acceptable salt thereof;

(25) a 2-amino-1,3-propanediol compound according to the above-mentioned(24), which is selected from the group consisting of 2-amino-2-3-(4-heptylcyclohexyl)propyl!-1,3-propanediol, 2-amino-2-4-(4-butylcyclohexyl)butyl!-1,3-propanediol, 2-amino-2-2-(4-octylcyclohexyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-nonylcyclohexyl)ethyl!-1,3-propanediol and 2-amino-2-2-(4-dodecylcyclohexyl)ethyl!-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(26) a 2-amino-1,3-propanediol compound according to the above-mentioned(12), having the formula ##STR20## wherein Rn is a 1-alkyl-substitutedpiperidin-4-ylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms intotal, and a pharmaceutically acceptable salt thereof;

(27) a 2-amino-1,3-propanediol compound according to the above-mentioned(26), which is selected from the group consisting of 2-amino-2-2-(1-octylpiperidin-4-yl)ethyl!-1,3-propanediol and 2-amino-2-2-(1-dodecylpiperidin-4-yl)ethyl!-1,3-propanediol, and apharmaceutically acceptable salt thereof;

(28) a 2-amino-1,3-propanediol compound according to the above-mentioned(12), having the formula ##STR21## wherein Ro is a thienylalkyl whereinthe alkyl moiety has 6 to 20 carbon atoms, an alkyl-substitutedthienylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms in total,pyridylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms or analkyl-substituted pyridylalkyl wherein the alkyl moiety has 6 to 20carbon atoms in total, and a pharmaceutically acceptable salt thereof;

(29) a 2-amino-1,3-propanediol compound according to the above-mentioned(28), which is selected from the group consisting of 2-amino-2-2-(5-octyl-2-thienyl)ethyl!-1,3-propanediol, 2-amino-2-2-(5-nonyl-2-thienyl)ethyl!-1,3-propanediol, 2-amino-2-2-(5-decyl-2-thienyl)ethyl!-1,3-propanediol, 2-amino-2-2-(5-dodecyl-2-thienyl)ethyl!-1,3-propanediol, 2-amino-2-13-(2-thienyl)tridecyl!-1,3-propanediol, 2-amino-2-2-(5-octyl-2-pyridyl)ethyl!-1,3-propanediol, 2-amino-2-2-(5-decyl-2-pyridyl)ethyl!-1,3-propanediol, 2-amino-2-13-(2-pyridyl)tridecyl!-1,3-propanediol, 2-amino-2-2-(2-octyl-5-pyridyl)ethyl!-1,3-propanediol, 2-amino-2-2-(2-decyl-5-pyridyl)ethyl!-1,3-propanediol and 2-amino-2-13-(3-pyridyl)tridecyl!-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(30) a 2-amino-1,3-propanediol compound according to the above-mentioned(1) or (2), having the formula ##STR22## wherein Rp is a phenylsubstituted by C6-C18 alkyl, a cycloalkyl, a heteroaryl or aheterocycle, and a pharmaceutically acceptable salt thereof;

(31) a 2-amino-1,3-propanediol compound according to the above-mentioned(30), having the formula ##STR23## wherein Rq is a phenyl substituted byC6-C18 alkyl, and a pharmaceutically acceptable salt thereof;

(32) a 2-amino-1,3-propanediol compound according to the above-mentioned(30) or (31), which is selected from the group consisting of2-amino-2-(4-decylphenyl)-1,3-propanediol,2-amino-2-(4-dodecylphenyl)-1,3-propanediol,2-amino-2-(4-tetradecylphenyl)-1,3-propanediol and2-amino-2-(4-hexadecylphenyl)-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(33) a 2-amino-1,3-propanediol compound according to the above-mentioned(1) or (2), having the formula ##STR24## wherein R¹ is an optionallysubstituted straight- or branched carbon chain which may have, in thechain, a bond, a hetero atom or a group selected from the groupconsisting of a double bond, a triple bond, oxygen, sulfur, sulfinyl,sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acyl oralkoxycarbonyl, and carbonyl, optionally substituted arylene, optionallysubstituted cycloalkylene, optionally-substituted heteroarylene and analicycle thereof, and which may be substituted, at the chain end(ω-position) thereof, by a double bond, a triple bond, optionallysubstituted aryl, optionally substituted cycloalkyl, optionallysubstituted heteroaryl or an alicycle thereof, an optionally substitutedaryl, an optionally substituted cycloalkyl, an optionally substitutedheteroaryl or an alicycle thereof, and

R² a, R³ a, R⁴ a and R⁵ a are the same or different and each is ahydrogen, an alkyl, an acyl or an alkoxycarbonyl;

wherein the optionally substituted straight- or branched carbon chainmay have a substituent selected from the group consisting of alkoxy,alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino,hydroxyimino, hydroxy, carboxy, optionally substituted aryl, optionallysubstituted aryloxy, optionally substituted cycloalkyl, optionallysubstituted heteroaryl and an alicycle thereof; and the aforementionedoptionally substituted arylene, optionally substituted cycloalkylene,optionally substituted heteroarylene, an alicycle thereof, optionallysubstituted aryl, optionally substituted aryloxy, optionally substitutedcycloalkyl, optionally substituted heteroaryl and an alicycle thereofmay have a substituent selected from the group consisting of alkoxy,alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxyand carboxy, and a pharmaceutically acceptable salt thereof;

(34) a 2-amino-1,3-propanediol compound according to the above-mentioned(33), having the formula ##STR25## wherein Rr is an alkyl optionallysubstituted by hydroxy and/or hydroxyimino which may have, in the chain,a double bond or carbonyl, and a pharmaceutically acceptable saltthereof;

(35) a 2-amino-1,3-propanediol compound according to the above-mentioned(33) or (34), which is selected from the group consisting of2-amino-2-(1,2,12-trihydroxy-4-octadecenyl)-1,3-propanediol,2-amino-2-(1,2-dihydroxy-4-octadecenyl)-1,3-propanediol,2-amino-2-(1,2-dihydroxyoctadecyl)-1,3-propanediol,2-amino-2-(1,12-dihydroxy-4-octadecenyl)-1,3-propanediol,2-amino-2-(1,2,4-trihydroxybutyl)-1,3-propanediol,2-amino-2-(1,2,12-trihydroxyoctadecyl)-1,3-propanediol and2-amino-2-(1,12-dihydroxyoctadecyl)-1,3-propanediol, and apharmaceutically acceptable salt thereof;

(36) a 2-amino-1,3-propanediol compound according to the above-mentioned(33), having the formula ##STR26## wherein Rs is a phenylalkylsubstituted by a straight- or branched chain C6-C14 alkyl optionallysubstituted by halogen, a straight- or branched chain C6-C14 alkoxyoptionally substituted by halogen or a straight- or branched chainC6-C14 alkenyloxy, and a pharmaceutically acceptable salt thereof;

(37) a 2-amino-1,3-propanediol compound according to the above-mentioned(36), which is selected from the group consisting of 2-amino-2-1-hydroxy-2-(4-octylphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-dodecylphenyl)-1-hydroxyethyl!-1,3-propanediol, 2-amino-2-2-(4-heptyloxyphenyl)-1-hydroxyethyl!-1,3-propanediol, 2-amino-2-1-hydroxy-2-(4-undecyloxyphenyl)ethyl!-1,3-propanediol, 2-amino-2-2-(4-(8-fluorooctyl)phenyl)-1-hydroxyethyl!-1,3-propanediol, 2-amino-2-2-(4-(12-fluorododecyl)phenyl)-1-hydroxyethyl!-1,3-propanediol,2-amino-2-2-(4-(7-fluoroheptyloxy)phenyl)-1-hydroxyethyl!-1,3-propanediol and2-amino-2-1-hydroxy-2-(4-(11-fluoroundecyloxy)phenyl)ethyl!-1,3-propanediol, and apharmaceutically acceptable salt thereof;

(38) a 2-amino-1,3-propanediol compound according to the above-mentioned(1) or (2), having the formula ##STR27## wherein Rt is an optionallysubstituted straight- or branched carbon chain which may have, in thechain, a bond, a hetero atom or a group selected from the groupconsisting of a double bond, a triple bond, oxygen, sulfur, sulfinyl,sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acyl oralkoxycarbonyl, carbonyl, optionally substituted arylene, optionallysubstituted cycloalkylene, optionally substituted heteroarylene and analicycle thereof, an optionally substituted aryl, an optionallysubstituted cycloalkyl, an optionally substituted heteroaryl or analicycle thereof, and

R² a, R³ a, R⁴ a and R⁵ a are the same or different and each is ahydrogen, an alkyl, an acyl or an alkoxycarbonyl;

wherein the optionally substituted straight- or branched carbon chainmay have a substituent selected from the group consisting of alkoxy,alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxy,carboxy, optionally substituted aryl, optionally substituted aryloxy,optionally substituted cycloalkyl, optionally substituted heteroaryl andan alicycle thereof; and the aforementioned optionally substitutedarylene, optionally substituted cycloalkylene, optionally substitutedheteroarylene, an alicycle thereof, optionally substituted aryl,optionally substituted aryloxy, optionally substituted cycloalkyl,optionally substituted heteroaryl and an alicycle thereof may have asubstituent selected from the group consisting of alkoxy, alkenyloxy,alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio,acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl,haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxy and carboxy, and apharmaceutically acceptable salt thereof;

(39) a 2-amino-1,3-propanediol compound according to the above-mentioned(38), having the formula ##STR28## wherein Ru is a phenyl substituted byalkyl having 4 to 16 carbon atoms, and a pharmaceutically acceptablesalt thereof;

(40) a 2-amino-1,3-propanediol compound according to the above-mentioned(38) or (39), which is selected from the group consisting of 2-amino-2-2-(4-octylphenyl)ethenyl!-1,3-propanediol, 2-amino-2-2-(4-decylphenyl)ethenyl!-1,3-propanediol, 2-amino-2-2-(4-dodecylphenyl)ethenyl!-1,3-propanediol and 2-amino-2-2-(4-tetradecylphenyl)ethenyl!-1,3-propanediol, and a pharmaceuticallyacceptable salt thereof;

(41) a 2-amino-1,3-propanediol compound according to the above-mentioned(1) or (2), having the formula ##STR29## wherein Rv is an optionallysubstituted aryl, an optionally substituted cycloalkyl, an optionallysubstituted heteroaryl or an alicycle thereof;

R² a, R³ a, R⁴ a and R⁵ a are the same or different and each is ahydrogen, an alkyl, an acyl or an alkoxycarbonyl;

X is an oxygen, a sulfur, a sulfinyl, a sulfonyl, --N(R⁶)-- where R⁶ ishydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl; and

α and β are 0 or an integer of 1-20 provided that α+β=5-20, wherein theoptionally substituted aryl, optionally substituted cycloalkyl,optionally substituted heteroaryl and an alicycle thereof may have asubstituent selected from the group consisting of alkyl, alkoxy,alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxyand carboxy, and a pharmaceutically acceptable salt thereof;

(42) a 2-amino-1,3-propanediol compound according to the above-mentioned(41), having the formula ##STR30## wherein Rw is a phenyl substituted byC4-C16 alkyl, and a pharmaceutically acceptable salt thereof;

(43) a 2-amino-1,3-propanediol compound according to the above-mentioned(41) or (42), which is selected from the group consisting of2-amino-2-(4-octylphenoxymethyl)-1,3-propanediol,2-amino-2-(4-decylphenoxymethyl)-1,3-propanediol,2-amino-2-(4-dodecylphenoxymethyl)-1,3-propanediol and2-amino-2-(4-tetradecylphenoxymethyl)-1,3-propanediol, and apharmaceutically acceptable salt thereof;

(44) a pharmaceutical composition comprising either one of theabove-mentioned compounds (1) through 4);

(45) an immunosuppressant comprising a 2-amino-1,3-propanediol compoundof the formula ##STR31## wherein R is an optionally substitutedstraight- or branched carbon chain which may have, in the chain, a bond,a hereto atom or a group selected from the group consisting of a doublebond, a triple bond, oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- whereR⁶ is hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl, carbonyl,optionally substituted arylene, optionally substituted cycloalkylene,optionally substituted heteroarylene and an alicycle thereof, and whichmay be substituted, at the chain end thereof, by a double bond, a triplebond, optionally substituted aryl, optionally substituted cycloalkyl,optionally substituted heteroaryl or an alicycle thereof, an optionallysubstituted aryl, an optionally substituted cycloalkyl, an optionallysubstituted heteroaryl or an alicycle thereof, and

R², R³, R⁴ and R⁵ are the same or different and each is a hydrogen, analkyl, an aralkyl, an acyl or an alkoxycarbonyl, or R⁴ and R⁵ may bebonded by an alkylene chain which may be substituted by alkyl, aryl oraralkyl;

wherein the optionally substituted straight- or branched carbon chainmay have a substituent selected from the group consisting of alkoxy,alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino,alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy,alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino,hydroxyimino, hydroxy, carboxy, optionally substituted aryl, optionallysubstituted aryloxy, optionally substituted cycloalkyl, optionallysubstituted heteroaryl and an alicycle thereof; the aforementionedoptionally substituted arylene, optionally substituted cycloalkylene,optionally substituted heteroarylene and an alicycle thereof may have asubstituent selected from the group consisting of alkoxy, alkenyloxy,alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio,acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl,haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxy and carboxy; andthe optionally substituted aryl, optionally substituted aryloxy,optionally substituted cycloalkyl, optionally substituted heteroaryl andan alicycle thereof may have a substituent selected from the groupconsisting of alkyl, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, haloalkoxy,nitro, halogen, amino, hydroxy and carboxy, and a pharmaceuticallyacceptable salt thereof;

(46) an immunosuppressant comprising a 2-amino-1,3-propanediol compoundor a pharmaceutically acceptable salt thereof according to either one ofthe aforementioned (1) through (43);

(47) a pharmaceutical agent according to the aforementioned (45) or(46), wherein the immunosuppressant is an agent for suppressingrejection;

(48) a pharmaceutical agent according to the aforementioned (45) or(46), wherein the immunosuppressant is an agent for the prevention andtreatment of autoimmune diseases; and

(49) a pharmaceutical agent according to the aforementioned (48),wherein the agent for the prevention and treatment of autoimmunediseases is an agent for the prevention and treatment of rheumatism.

The groups represented by respective symbols in the presentspecification are explained in the following.

The carbon chain at R, R¹, R¹ a or Rt is a straight- or branched carbonchain having 1 to 30 carbon atoms and is exemplified by methyl, ethyl,propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl,tert-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl,tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl,nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl,hexacosyl, heptacosyl, octacosyl, nonacosyl and triacontyl.

The arylene at R, R¹ or Rt is exemplified by phenylene and naphthylene,with preference given to phenylene.

The cycloalkylene at R, R¹, R¹ a or Rt is that having 3 to 10 carbonatoms and is exemplified by cyclopropylene, cyclobutylene,cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene,cyclononylene and cyclodecylene, with preference given to cyclohexylene.

The heteroarylene at R, R¹ or Rt is a 5- or 6-membered heteroaryleneoptionally having, in the ring, 1 or 2 hetero atoms selected fromnitrogen atom, oxygen atom and sulfur atom and is exemplified bythiophen-(2,4-, 2,5- or 3,4-)ylene, furan-(2,4-, 2,5- or 3,4-)ylene,pyrrol-(1,3-, 2,4-, 2,5- or 3,4-)ylene, imidazol-(1,4-, 2,4- or2,5-)ylene, thiazol-(2,4- or 2,5-)ylene, isothiazol-(3,4- or 3,5-)ylene,oxazol-(2,4- or 2,5-)ylene, isoxazol-(3,4- or 3,5-)ylene, pyridin-(2,4-,2,5-, 2,6- or 3,5-)ylene, pyrimidin-(2,4- or 2,5-)ylene,pyrazin-2,5-ylene, pyridazin-(3,5- or 3,6-)ylene and pyran-(2,4-, 2,5-or 2,6-)ylene, with preference given to thiophen-2,5-ylene andpyridin-2,5-ylene.

The alicycle of the aforementioned heteroarylene at R, R¹ or Rt is theaforementioned heteroarylene when saturated and is exemplified bypyrrolidine-(1,3-, 2,4-, 2,5- or 3,4-)ylene, piperidine-(1,4-, 2,4-,2,5-, 2,6- or 3,5-)ylene, piperazine-1,4-ylene, morpholine-2,4 or3,4-ylene and thiomorpholine-2,4 or 3,4-ylene.

The aryl at R, R¹, Rt or Rv is exemplified by phenyl and naphthyl, withpreference given to phenyl.

The cycloalkyl at R, R¹, R¹ a, R¹ b, Rp, Rt or Rv is cycloalkyl having 3to 10 carbon atoms and includes, for example, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl andcyclodecyl, with preference given to cyclohexyl.

The heteroaryl at R, R¹, Rp, Rt or Rv is a 5- or 6-membered heteroaryloptionally having, in the ring, 1 to 4 hetero atoms selected fromnitrogen atom, oxygen atom and sulfur atom and includes, for example,monocyclic heteroaryl such as thienyl(2-thienyl, 3-thienyl),furyl(2-furyl, 3-furyl), pyrrolyl(1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl),imidazolyl(2-imidazolyl, 4-imidazolyl), pyrazolyl(3-pyrazolyl,4-pyrazolyl), triazolyl, tetrazolyl, thiazolyl(2-thiazolyl,4-thiazolyl), isothiazolyl(3-isothiazolyl, 4-isothiazolyl),oxazolyl(2-oxazolyl, 4-oxazolyl), isooxazolyl(3-isooxazolyl,4-isooxazolyl), pyridyl(2-pyridyl, 3-pyridyl, 4-pyridyl), pyrazinyl,pyrimidinyl(2-pyrimidinyl, 4-pyrimidinyl), pyridazinyl(3-pyridazinyl,4-pyridazinyl) or pyranyl(2-pyranyl, 3-pyranyl, 4-pyranyl), and bicyclicheteroaryl such as indolyl(2-indolyl, 3-indolyl), quinolyl(2-quinolyl,3-quinolyl), isoquinolyl(1-isoquinolyl, 3-isoquinolyl),benzofuranyl(2-benzofuranyl, 3-benzofuranyl),benzothienyl(2-benzothienyl, 3-benzothienyl), 1H-benzimidazol-2-yl orchromenyl(2-chromenyl, 3-chromenyl, 4-chromenyl).

The alicycle of the aforementioned heteroaryl at R, R¹, Rt or Rv is theabove-mentioned monocyclic heteroaryl when saturated and includes, forexample, pyrrolidinyl(1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl),piperidyl(2-piperidyl, 3-piperidyl, 4-piperidyl), piperidino,piperazinyl, morpholinyl and thiomorpholinyl.

The heterocycle at Rp means an alicycle of heteroaryl.

The alkyl at R¹ b or Rr is a straight- or branched chain alkyl having 1to 30 carbon atoms and is exemplified by methyl, ethyl, propyl,isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, tert-pentyl,hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl,tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl,icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,heptacosyl, octacosyl, nonacosyl and triacontyl.

The straight- or branched chain alkyl having 12 to 22 carbon atoms at Raand the straight- or branched chain alkyl having 13 to 20 carbon atomsat Rb or Rc are the above-mentioned alkyl having the specified numbersof carbon atoms.

The alkenyl at R¹ b is a straight- or branched chain alkenyl having 2 to30 carbon atoms and includes, for example, ethenyl, propenyl,isopropenyl, butenyl, isobutenyl, pentenyl, isopentenyl, hexenyl,heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl,tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl,nonadecenyl, icosenyl, henicosenyl, docosenyl, tricosenyl, tetracosenyl,pentacosenyl, hexacosenyl, heptacosenyl, octacosenyl, nonacosenyl andtriacontenyl.

The alkynyl at R¹ b is a straight- or branched chain alkynyl having 2 to30 carbon atoms and includes, for example, ethynyl, propynyl,isopropynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl,decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl,hexadecynyl, heptadecynyl, octadecynyl, nonadecynyl, icosynyl,henicosynyl, docosynyl, tricosynyl, tetracosynyl, pentacosynyl,hexacosynyl, heptacosynyl, octacosynyl, nonacosynyl and triacontynyl.

The phenylalkyl at Rd, Re, Rf, Rg, Ri, Rk or Rs is that where the alkylmoiety is a straight- or branched chain alkyl having 1 to 30 carbonatoms and includes, for example, benzyl, 1-phenylethyl, 2-phenylethyl,1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 4-phenylbutyl,5-phenylpentyl, 6-phenylhexyl, 7-phenylheptyl, 8-phenyloctyl,9-phenylnonyl, 10-phenyldecyl, 11-phenylundecyl, 12-phenyldodecyl,13-phenyltridecyl, 14-phenyltetradecyl, 15-phenylpentadecyl,16-phenylhexadecyl, 17-phenylheptadecyl, 18-phenyloctadecyl,19-phenylnonadecyl, phenylicosyl, 21-phenylhenicosyl, 22-phenyldocosyl,23-phenyltricosyl, 24-phenyltetracosyl, 25-phenylpentacosyl,26-phenylhexacosyl, 27-phenylheptacosyl, 28-phenyloctacosyl,29-phenylnonacosyl and 30-phenyltriacontyl.

The phenylalkyl at Re, Rf, Rg or Rh where the alkyl moiety has 6 to 20carbon atoms and that at Rj or Rl where the alkyl moiety has 2 to 6carbon atoms are the above-mentioned phenylalkyl having the specifiednumbers of carbon atoms.

The phenylalkoxyalkyl at Rh where the alkyl moiety and alkoxy moietyhave 6 to 20 carbon atoms in total is exemplified by5-phenylmethyloxypentyl, 6-phenylmethyloxyhexyl,7-phenylmethyloxyheptyl, 8-phenylmethyloxyoctyl, 9-phenylmethyloxynonyl,10-phenylmethyloxydecyl, 12-phenylmethyloxydodecyl,14-phenylmethyloxytetradecyl, 16-phenylmethyloxyhexadecyl,18-phenylmethyloxyoetadecyl, 2-(8-phenyloctyloxy)ethyl,3-(8-phenyloctyloxy)propyl, 4-(8-phenyloctyloxy)butyl,5-(8-phenyloctyloxy)pentyl, 6-(8-phenyloctyloxy)hexyl and7-(8-phenyloctyloxy)heptyl.

The phenoxyalkyl at Rh where the alkyl moiety has 6 to 20 carbon atomsis exemplified by 6-phenoxyhexyl, 7-phenoxyheptyl, 8-phenoxyoctyl,9-phenoxynonyl, 10-phenoxydecyl, 11-phenoxyundecyl, 12-phenoxydodecyl,13-phenoxytridecyl, 14-phenoxytetradecyl, 15-phenoxypentadecyl,16-phenoxyhexadecyl, 17-phenoxyheptadecyl, 18-phenoxyoctadecyl,19-phenoxynonadecyl and 20-phenoxyicosyl.

The phenoxyalkoxyalkyl at Rh where the alkyl moiety and alkoxy moietyhave 6 to 20 carbon atoms in total is exemplified by5-(2-phenoxyethyloxy)pentyl, 6-(2-phenoxyethyloxy)hexyl,7-(2-phenoxyethyloxy)heptyl, 8-(2-phenoxyethyloxy)octyl,5-(3-phenoxypropyloxy)pentyl, 6-(3-phenoxypropyloxy)hexyl,7-(3-phenoxypropyloxy)heptyl, 8-(3-phenoxypropyloxy)octyl,5-(4-phenoxybutyloxy)pentyl, 6-(4-phenoxybutyloxy)hexyl,7-(4-phenoxybutyloxy)heptyl, 8-(4-phenoxybutyloxy)octyl,5-(6-phenoxyhexyloxy)pentyl, 6-(6-phenoxyhexyloxy)hexyl,7-(6-phenoxyhexyloxy)heptyl and 8-(6-phenoxyhexyloxy)octyl.

The cycloalkylalkyl at Rd, Re, Rf or Rg is that where the alkyl moietyis a straight- or branched chain alkyl having 1 to 30 carbon atoms andthe cycloalkyl moiety is a cycloalkyl having 3 to 10 carbon atoms, andis exemplified by cyclohexylmethyl, 1-cyclohexylethyl,2-cyclohexylethyl, 1-cyclohexylpropyl, 2-cyclohexylpropyl,3-cyclohexylpropyl, 4-cyclohexylbutyl, 5-cyclohexylpentyl,6-cyclohexylhexyl, 7-cyclohexylheptyl, 8-cyclohexyloctyl,9-cyclohexylnonyl, 10-cyclohexyldecyl, 11-cyclohexylundecyl,12-cyclohexyldodecyl, 13-cyclohexyltridecyl, 14-cyclohexyltetradecyl,15-cyclohexylpentadecyl, 16-cyclohexylhexadecyl,17-cyclohexylheptadecyl, 18-cyclohexyloctadecyl, 19-cyclohexylnonadecyl,20-cyclohexylicosyl, 21-cyclohexylhenicosyl, 22-cyclohexyldocosyl,23-cyclohexyltricosyl, 24-cyclohexyltetracosyl, 25-cyclohexylpentacosyl,26-cyclohexylhexacosyl, 27-cyclohexylheptacosyl, 28-cyclohexyloctacosyl,29-cyclohexylnonacosyl and 30-cyclohexyltriacontyl.

The cycloalkylalkyl at Re, Rf or Rg where the alkyl moiety has 6 to 20carbon atoms is the above-mentioned cycloalkylalkyl having the specifiednumbers of carbon atoms.

The alkyl-substituted cycloalkylalkyl at Rm where the alkyl moiety has 6to 20 carbon atoms is exemplified by 3-(4-heptylcyclohexyl)propyl,4-(4-butylcyclohexyl)butyl, 2-(4-octylcyclohexyl)ethyl,2-(4-nonylcyclohexyl)ethyl and 2-(4-dodecylcyclohexyl)ethyl.

The heteroarylalkyl at Rd, Re, Rf or Rg is that where the alkyl moietyis a straight- or branched chain alkyl having 1 to 30 carbon atoms andis exemplified by thienylalkyl and pyridylalkyl such as (thienyl orpyridyl)methyl, 1-(thienyl or pyridyl)ethyl, 2-(thienyl orpyridyl)ethyl, 1-(thienyl or pyridyl)propyl, 2-(thienyl orpyridyl)propyl, 3-(thienyl or pyridyl)propyl, 4-(thienyl orpyridyl)butyl, 5-(thienyl or pyridyl)pentyl, 6-(thienyl orpyridyl)hexyl, 7-(thienyl or pyridyl)heptyl, 8-(thienyl orpyridyl)octyl, 9-(thienyl or pyridyl)nonyl, 10-(thienyl orpyridyl)decyl, 11-(thienyl or pyridyl)undecyl, 12-(thienyl orpyridyl)dodecyl, 13-(thienyl or pyridyl)tridecyl, 14-(thienyl orpyridyl)tetradecyl, 15-(thienyl or pyridyl)pentadecyl, 16-(thienyl orpyridyl)hexadecyl, 17-(thienyl or pyridyl)heptadecyl, 18-(thienyl orpyridyl)octadecyl, 19-(thienyl or pyridyl)nonadecyl, 20-(thienyl orpyridyl)icosyl, 21-(thienyl or pyridyl)henicosyl, 22-(thienyl orpyridyl)docosyl, 23-(thienyl or pyridyl)tricosyl, 24-(thienyl orpyridyl)tetracosyl, 25-(thienyl or pyridyl)pentacosyl, 26-(thienyl orpyridyl)hexacosyl, 27-(thienyl or pyridyl)heptacosyl, 28-(thienyl orpyridyl)octacosyl, 29-(thienyl or pyridyl)nonacosyl and 30-(thienyl orpyridyl)triacontyl.

The heteroarylalkyl at Re, Rf or Rg where the alkyl moiety has 6 to 20carbon atoms is the above-mentioned heteroarylalkyl having the specifiednumbers of carbon atoms.

The alkyl-substituted thienylalkyl at Ro where the alkyl moiety has 6 to20 carbon atoms in total is exemplified by 2-(5-octyl-2-thienyl)ethyl,2-(5-nonyl-2-thienyl)ethyl, 2-(5-decyl-2-thienyl)ethyl and2-(5-dodecyl-2-thienyl)ethyl.

The thienylalkyl at Ro where the alkyl moiety has 6 to 20 carbon atomsis thienylalkyl from among the above-mentioned heteroarylalkyls.Preferred is 13-(2-thienyl)tridecyl.

The alkyl-substituted pyridylalkyl at Ro where the alkyl moiety has 6 to20 carbon atoms in total is exemplified by 2-(5-octyl-2-pyridyl)ethyl,2-(5-decyl-2-pyridyl)ethyl, 2-(2-octyl-5-pyridyl)ethyl and2-(2-decyl-5-pyridyl)ethyl.

The pyridylalkyl at Ro where the alkyl moiety has 6 to 20 carbon atomsis pyridylalkyl from among the above-mentioned heteroarylalkyls.Preferred are 13-(2-pyridyl)tridecyl and 13-(3-pyridyl)tridecyl.

The heterocyclic alkyl at Rd, Re, Rf or Rg where the alkyl moiety is astraight- or branched chain alkyl having 1 to 30 carbon atoms andheterocyclic means an alicycle of heteroaryl, is exemplified by4-piperidylmethyl, 1-(4-piperidyl)ethyl, 2-(4-piperidyl)ethyl,1-(4-piperidyl)propyl, 2-(4-piperidyl)propyl, 3-(4-piperidyl)propyl,4-(4-piperidyl)butyl, 5-(4-piperidyl)pentyl, 6-(4-piperidyl)hexyl,7-(4-piperidyl)heptyl, 8-(4-piperidyl)octyl, 9-(4-piperidyl)nonyl,10-(4-piperidyl)decyl, 11-(4-piperidyl)undecyl, 12-(4-piperidyl)dodecyl,13-(4-piperidyl)tridecyl, 14-(4-piperidyl)tetradecyl,15-(4-piperidyl)pentadecyl, 16-(4-piperidyl)hexadecyl,17-(4-piperidyl)heptadecyl, 18-(4-piperidyl)octadecyl,19-(4-piperidyl)nonadecyl, 20-(4-piperidyl)icosyl,21-(4-piperidyl)henicosyl, 22-(4-piperidyl)docosyl,23-(4-piperidyl)tricosyl, 24-(4-piperidyl)tetracosyl,25-(4-piperidyl)pentacosyl, 26-(4-piperidyl)hexacosyl,27-(4-piperidyl)heptacosyl, 28-(4-piperidyl)octacosyl,29-(4-piperidyl)nonacosyl and 30-(4-piperidyl)triacontyl.

The heterocyclic alkyl at Re, Rf or Rg where the alkyl moiety has 6 to20 carbon atoms is the above-mentioned heterocyclic alkyl having thespecified numbers of carbon atoms.

The 1-alkyl-substituted piperidin-4-ylalkyl at Rn where the alkyl moietyhas 6 to 20 carbon atoms in total is, for example,2-(1-octylpiperidin-4-yl)ethyl and 2-(1-dodecylpiperidin-4-yl)ethyl.

The alkyl as a substitutent at R, R¹ b, Rd, Rm, Rn, Ro or Rv is astraight- or branched chain alkyl having 1 to 20 carbon atoms and isexemplified by methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl,octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl,hexadecyl, heptadecyl, octadecyl, nonadecyl and icosyl.

The straight- or branched chain alkyl having 6 to 20 carbon atoms as asubstituent at Re or Rf, the straight- or branched chain alkyl having 6to 14 carbon atoms as a substituent at Rg, Ri, Rj or Rs, the alkylhaving 6 to 18 carbon atoms as a substituent at Rp or Rq and the alkylhaving 4 to 16 carbon atoms as a substituent at Ru or Rw are theabove-mentioned alkyls having the specified numbers of carbon atoms.

The alkoxy as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rt orRv is a straight- or branched chain alkoxy having 1 to 20 carbon atomsand is exemplified by methoxy, ethoxy, propoxy, isopropoxy, butoxy,isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy,tert-pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy,undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy,hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy and icosyloxy.

The straight- or branched chain alkoxy having 6 to 20 carbon atoms as asubstituent at Re or Rf and the straight- or branched chain alkoxyhaving 6 to 14 carbon atoms as a substituent at Rg, Ri, Rj or Rs are theabove-mentioned alkoxys having the specified numbers of carbon atoms.

The alkenyloxy as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rtor Rv is that where the alkenyl moiety is a straight- or branched chainalkenyl having 2 to 20 carbon atoms and is exemplified by vinyloxy,propenyloxy, isopropenyloxy, butenyloxy, isobutenyloxy, pentenyloxy,isopentenyloxy, hexenyloxy, heptenyloxy, octenyloxy, nonenyloxy,decenyloxy, undecenyloxy, dodecenyloxy, tridecenyloxy, tetradecenyloxy,pentadecenyloxy, hexadecenyloxy, heptadecenyloxy, octadecenyloxy,nonadecenyloxy and icosenyloxy.

The straight- or branched chain alkenyloxy having 6 to 20 carbon atomsas a substituent at Re or Rf and the straight- or branched chainalkenyloxy having 6 to 14 carbon atoms as a substituent at Rg, Ri, Rj orRs are the above-mentioned alkenyloxys having the specified numbers ofcarbon atoms.

The alkynyloxy as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rtor Rv is that where the alkynyl moiety is a straight- or branched chainalkynyl having 2 to 20 carbon atoms and is exemplified by ethynyloxy,propynyloxy, butynyloxy, pentynyloxy, hexynyloxy, heptynyloxy,octynyloxy, nonynyloxy, decynyloxy, undecynyloxy, dodecynyloxy,tridecynyloxy, tetradecynyloxy, pentadecynyloxy, hexadecynyloxy,heptadecynyloxy, octadecynyloxy, nonadecynyloxy and icosynyloxy.

The aralkyloxy as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rtor Rv is that wherein the aralkyl is that where the alkyl moiety is astraight- or branched chain alkyl having 1 to 20 carbon atoms and thearalkyloxy is exemplified by phenylalkoxy such as benzyloxy,2-phenethyloxy, 1-phenylethyloxy, 1-phenylpropyloxy, 2-phenylpropyloxy,3-phenylpropyloxy, 4-phenylbutyloxy, 5-phenylpentyloxy,6-phenylhexyloxy, 7-phenylheptyloxy, 8-phenyloctyloxy, 9-phenylnonyloxy,10-phenyldecyloxy, 11-phenylundecyloxy, 12-phenyldodecyloxy,13-phenyltridecyloxy or 14-phenyltetradecyloxy, and naphthylalkoxy suchas naphthylmethyl or 2-naphthylethyl, with preference given tophenylalkoxy.

The phenylalkoxy as a substituent at Re, Rf, Rg or Rk is phenylalkoxy ofthe aforementioned aralkyloxy.

The phenylalkoxy as a substituent at Rl where the alkoxy moiety has 2 to8 carbon atoms is phenylalkoxy of the aforementioned aralkyloxy, havingthe specified numbers of carbon atoms.

The alkylenedioxy as a substituent at R, R¹, R¹ a, Rd, Rt or Rv isalkylenedioxy where the alkylene moiety is a straight- or branched chainalkylene having 1 to 20 carbon atoms and is exemplified bymethylenedioxy, ethylenedioxy, propylenedioxy, trimethylenedioxy,butylenedioxy, 1,2-dimethylethylenedioxy, pentamethylenedioxy,hexamethylenedioxy, heptamethylenedioxy, octamethylenedioxy,nonamethylenedioxy, decamethylenedioxy, undecamethylenedioxy,dodecamethylenedioxy, tridecamethylenedioxy, tetradecamethylenedioxy,pentadecamethylenedioxy, hexadecamethylenedioxy,heptadecamethylenedioxy, octadecamethylenedioxy, nonadecamethylenedioxyand icosamethylenedioxy, with preference given to methylenedioxy andethylenedioxy.

The acyl as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rt or Rvis optionally substituted alkanoyl or aroyl, in which alkanoyl is astraight- or branched chain alkanoyl having 1 to 20 carbon atoms, and isexemplified by formyl, acetyl, propionyl, butyryl, isobutyryl,pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl,undecanoyl, dodecanoyl, tridecanoyl, tetradecanoyl, pentadecanoyl,hexadecanoyl, heptadecanoyl, octadecanoyl, nonadecanoyl and icosanoyl,where alkanoyl may be substituted by phenyl. Examples of the alkanoyloptionally substituted by phenyl include phenylacetyl andphenylpropionyl. Examples of aroyl include benzoyl.

The alkylamino as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rtor Rv is that-where the alkyl moiety is a straight -or branched chainalkyl having 1 to 20 carbon atoms, and is exemplified by methylamino,ethylamino, propylamino, isopropylamino, butylamino, isobutylamino,sec-butylamino, tert-butylamino, pentylamino, isopentylamino,tert-pentylamino, hexylamino, heptylamino, octylamino, nonylamino,decylamino, undecylamino, dodecylamino, tridecylamino, tetradecylamino,pentadecylamino, hexadecylamino, heptadecylamino, octadecylamino,nonadecylamino and icosylamino.

The alkylthio as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rtor Rv is that where the alkyl moiety is a straight- or branched chainalkyl having 1 to 20 carbon atoms, and is exemplified by methylthio,ethylthio, propylthio, isopropylthio, butylthio, isobutylthio,sec-butylthio, tert-butylthio, pentylthio, isopentylthio,tert-pentylthio, hexylthio, heptylthio, octylthio, nonylthio, decylthio,undecylthio, dodecylthio, tridecylthio, tetradecylthio, pentadecylthio,hexadecylthio, heptadecylthio, octadecylthio, nonadecylthio andicosylthio.

The acylamino as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rtor Rv is that where the acyl moiety is a straight- or branched chainalkanoyl having 1 to 20 carbon atoms, and is exemplified by formylamino,acetylamino, propionylamino, butyrylamino, isobutyrylamino,pentanoylamino, pivaloylamino, hexanoylamino, heptanoylamino,octanoylamino, nonanoylamino, decanoylamino, undecanoylamino,dodecanoylamino, tridecanoylamino, tetradecanoylamino,pentadecanoylamino, hexadecanoylamino, heptadecanoylamino,octadecanoylamino, nonadecanoylamino and icosanoylamino.

The alkoxycarbonyl as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re,Rf, Rt or Rv is that where the alkoxy moiety is an optionallysubstituted straight- or branched chain alkoxy having 1 to 20 carbonatoms, and is exemplified by methoxycarbonyl, ethoxycarbonyl,propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl,tert-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl,tert-pentyloxycarbonyl, hexyloxycarbonyl, heptyloxycarbonyl,octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl,undecyloxycarbonyl, dodecyloxycarbonyl, tridecyloxycarbonyl,tetradecyloxycarbonyl, pentadecyloxycarbonyl, hexadecyloxycarbonyl,heptadecyloxycarbonyl, octadecyloxycarbonyl, nonadecyloxycarbonyl andicosyloxycarbonyl, which may be substituted by phenyl. Examples thereofinclude benzyloxycarbonyl.

The alkoxycarbonylamino as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd,Re, Rf, Rt or Rv is that where the alkoxy moiety is an optionallysubstituted straight- or branched chain alkoxy having 1 to 20 carbonatoms, and is exemplified by methoxycarbonylamino, ethoxycarbonylamino,propoxycarbonylamino, isopropoxycarbonylamino, butoxycarbonylamino,isobutoxycarbonylamino, tert-butoxycarbonylamino,pentyloxycarbonylamino, isopentyloxycarbonylamino,tert-pentyloxycarbonylamino, hexyloxycarbonylamino,heptyloxycarbonylamino, octyloxycarbonylamino, nonyloxycarbonylamino,decyloxycarbonylamino, undecyloxycarbonylamino, dodecyloxycarbonylamino,tridecyloxycarbonylamino, tetradecyloxycarbonylamino,pentadecyloxycarbonylamino, hexadecyloxycarbonylamino,heptadecyloxycarbonylamino, octadecyloxycarbonylamino,nonadecyloxycarbonylamino and icosyloxycarbonylamino, which may besubstituted by phenyl. Examples thereof include benzyloxycarbpnylamino.

The acyloxy as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re, Rf, Rt orRv is that where the acyl moiety is a straight- or branched chainalkanoyl having 2 to 20 carbon atoms, and is exemplified by acetoxy,propionyloxy, butyryloxy, isobutyryloxy, pivaloyloxy, pentanoyloxy,hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy,undecanoyloxy, dodecanoyloxy, tridecanoyloxy, tetradecanoyloxy,pentadecanoyloxy, hexadecanoyloxy, heptadecanoyloxy, octadecanoyloxy,nonadecanoyloxy and icosanoyloxy.

The alkylcarbamoyl as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rd, Re,Rf, Rt or Rv is that where the alkyl moiety is a straight- or branchedchain alkyl having 1 to 20 carbon atoms, and is exemplified bymethylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, butylcarbamoyl,pentylcarbamoyl, hexylcarbamoyl, heptylcarbamoyl, octylcarbamoyl,nonylcarbamoyl, decylcarbamoyl, undecylcarbamoyl, dodecylcarbamoyl,tridecylcarbamoyl, tetradecylcarbamoyl, pentadecylcarbamoyl,hexadecylcarbamoyl, heptadecylcarbamoyl, octadecylcarbamoyl,nonadecylcarbamoyl and icosylcarbamoyl.

The haloalkyl as a substituent at R, R¹, R¹ a, R¹ b, Rd, Rt or Rv isthat where the alkyl moiety is a straight- or branched chain alkylhaving 1 to 20 carbon atoms, and is exemplified by fluoromethyl,trifluoromethyl, chloromethyl, 2,2,2-trifluoroethyl, perfluoroethyl,3-chloropropyl, 3-fluoropropyl, 4-chlorobutyl, 4-fluorobutyl,5-chloropentyl, 6-chlorohexyl, 6-fluorohexyl, 7-chloroheptyl,7-fluoroheptyl, 8-fluorooctyl, 9-fluorononyl, 10-fluorodecyl,11-fluoroundecyl, 12-fluorododecyl, 13-fluorotridecyl,14-fluorotetradecyl, 15-fluoropentadecyl, 16-fluorohexadecyl,17-fluoroheptadecyl, 18-fluorooctadecyl, 19-fluorononadecyl and20-fluoroicosyl.

The haloalkoxy as a substituent at R, R¹, Rd, Rt or Rv has 1 to 20carbon atoms, and is exemplified by chloromethoxy, bromomethoxy,fluoromethoxy, dichloromethoxy, dibromomethoxy, difluoromethoxy,2-chloroethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy, 3-chloropropoxy,3-fluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 4-chlorobutoxy,4-fluorobutoxy, 5-chloropentyloxy, 5-fluoropentyloxy, 6-chlorohexyloxy,6-fluorohexyloxy, 7-chloroheptyloxy, 7-fluoroheptyloxy,8-fluorooctyloxy, 9-fluorononyloxy, 10-fluorodecyloxy,11-fluoroundecyloxy, 12-fluorododecyloxy, 13-fluorotridecyloxy,14-fluorotetradecyloxy, 15-fluoropentadecyloxy, 16-fluorohexadecyloxy,17-fluoroheptadecyloxy, 18-fluorooctadecyloxy, 19-fluorononadecyloxy and20-fluoroicosyloxy.

The halogen as a substituent at R, R¹, R¹ a, R¹ b, Ra, Rb, Rc, Rd, Re,Rf, Rg, Ri, Rj, Rs, Rt or Rv is exemplified by fluorine, chlorine,bromine and iodine.

The aryl as a substituent at R, R¹ or Rt is exemplified by phenyl andnaphthyl, with preference given to phenyl.

The aryloxy as a substituent at R, R¹ or Rt is exemplified by phenoxyand naphthyloxy, with preference given to phenoxy.

The cycloalkyl as a substituent at R, R¹, R¹ a, R¹ b or Rt is thathaving 3 to 10 carbon atoms and is exemplified by cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyland cyclodecyl, with preference given to cyclohexyl.

The heteroaryl as a substituent at R, R¹ or Rt is a 5- or 6-memberedheteroaryl optionally having, in the ring, 1 to 4 hetero atoms selectedfrom nitrogen atom, oxygen atom and sulfur atom and includes, forexample, monocyclic heteroaryl such as thienyl(2-thienyl, 3-thienyl),furyl(2-furyl, 3-furyl), pyrrolyl(1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl),imidazolyl(2-imidazolyl, 4-imidazolyl etc.), pyrazolyl(3-pyrazolyl,4-pyrazolyl etc.), triazolyl, tetrazolyl, thiazolyl(2-thiazolyl,4-thiazolyl), isothiazolyl(3-isothiazolyl, 4-isothiazolyl),oxazolyl(2-oxazolyl, 4-oxazolyl), isoxazolyl(3-isooxazolyl,4-isooxazolyl), pyridyl(2-pyridyl, 3-pyridyl, 4-pyridyl), pyrazinyl,pyrimidinyl(2-pyrimidinyl, 4-pyrimidinyl), pyridazinyl(3-pyridazinyl,4-pyridazinyl) and pyranyl(2-pyranyl, 3-pyranyl, 4-pyranyl), andbicyclic heteroaryl such as indolyl(2-indolyl, 3-indolyl),quinolyl(2-quinolyl, 3-quinolyl), isoquinolyl(1-isoquinolyl,3-isoquinolyl), benzofuranyl(2-benzofuranyl, 3-benzofuranyl),benzothienyl(2-benzothienyl, 3-benzothienyl), 1H-benzimidazol-2-yl orchromenyl(2-chromenyl, 3-chromenyl, 4-chromenyl).

The alicycle of the aforementioned heteroaryl as a substituent at R, R¹or Rt is the above-mentioned monocyclic heteroaryl when saturated suchas pyrrolidinyl(1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl),piperidyl(2-piperidyl, 3-piperidyl, 4-piperidyl), piperidino,piperazinyl, morpholinyl or thiomorpholinyl.

The carbon chain as a substituent at R¹ a is a straight- or branchedcarbon chain having 1 to 30 carbon atoms such as methyl, ethyl, propyl,isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, tert-pentyl,hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl,tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl,icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,heptacosyl, octacosyl, nonacosyl or triacontyl.

The alkenyl as a substituent at R¹ b is a straight- or branched chainalkenyl having 2 to 20 carbon atoms such as ethenyl, propenyl,isopropenyl, butenyl, isobutenyl, pentenyl, isopentenyl, hexenyl,heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl,tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl,nonadecenyl or icosenyl.

The alkynyl as a substituent at R¹ b is a straight- or branched chainalkynyl having 2 to 20 carbon atoms such as ethynyl, propynyl,isopropynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl,decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl,hexadecynyl, heptadecynyl, octadecynyl, nonadecynyl or icosynyl.

The haloaralkyloxy as a substituent at Rd is that including aralkylwhere the alkyl moiety is a straight- or branched chain alkyl having 1to 20 carbon atoms, and is exemplified by halophenylalkoxy such as4-fluorobenzyloxy, 2-(4-fluorophenyl)ethyloxy,1-(4-fluorophenyl)ethyloxy, 1-(4-fluorophenyl)propyloxy,2-(4-fluorophenyl)propyloxy, 3-(4-fluorophenyl)propyloxy,4-(4-fluorophenyl)butyloxy, 5-(4-fluorophenyl)pentyloxy,6-(4-fluorophenyl)hexyloxy, 7-(4-fluorophenyl)heptyloxy,8-(4-fluorophenyl)octyloxy, 9-(4-fluorophenyl)nonyloxy,10-(4-fluorophenyl)decyloxy, 11-(4-fluorophenyl)undecyloxy,12-(4-fluorophenyl)dodecyloxy, 13-(4-fluorophenyl)tridecyloxy or14-(4-fluorophenyl)tetradecyloxy, and halonaphthylalkoxy such as(7-fluoro-2-naphthyl)methyloxy or 2-(7-fluoro-2-naphthyl)ethyloxy, withpreference given to halophenylalkoxy.

The halophenylalkoxy as a substituent at Re, Rf, Rg or Rk is that of theaforementioned haloaralkyloxy.

The halophenylalkoxy as a substituent at Rl, where the alkoxy moiety has2 to 8 carbon atoms, is halophenylalkoxy of the aforementionedhaloaralkyloxy, having the specified numbers of carbon atoms.

The aralkyloxyalkyl as a substituent at Rd is that where the alkylmoiety and the alkyl moiety of the aralkyl are straight- or branchedchain alkyls having 1 to 20 carbon atoms and have 2 to 20 carbon atomsin total, and is exemplified by phenylalkoxyalkyl such asphenylmethyloxymethyl, 2-phenylethyloxymethyl, 3-phenylpropyloxymethyl,4-phenylbutyloxymethyl, 5-phenylpentyloxymethyl, 6-phenylhexyloxymethyl,7-phenylheptyloxymethyl, 8-phenyloctyloxymethyl, 9-phenylnonyloxymethyl,10-phenyldecyloxymethyl, 12-phenyldodecyloxymethyl,14-phenyltetradecyloxymethyl, 16-phenylhexadecyloxymethyl or18-phenyloctadecyloxymethyl, and naphthylalkoxyalkyl such as4-(2-naphthyl)butyloxymethyl, 5-(2-naphthyl)pentyloxymethyl or6-(2-naphthyl)hexyloxymethyl, with preference given tophenylalkoxyalkyl.

The phenylalkoxyalkyl as a substituent at Re, Rf, Rg or Rk is that ofthe aforementioned aralkyloxyalkyl.

The phenylalkoxyalkyl as a substituent at Rl, where the alkoxy moietyand the alkyl moiety have 2 to 8 carbon atoms in total, isphenylalkoxyalkyl of the aforementioned aralkyloxyalkyl, having thespecified numbers of carbon atoms, in which the carbon number of thealkoxy moiety and the alkyl moiety is respectively 1 to 7, with totalbeing 2 to 8.

The phenoxylalkyl as a substituent at Rd, Re, Rf, Rg or Rk is that wherethe alkyl moiety is a straight- or branched chain alkyl having 1 to 20carbon atoms and is exemplified by phenoxymethyl, 1-phenoxyethyl,2-phenoxyethyl, 1-phenoxypropyl, 2-phenoxypropyl, 3-phenoxypropyl,4-phenoxybutyl, 5-phenoxypentyl, 6-phenoxyhexyl, 7-phenoxyheptyl,8-phenoxyoctyl, 9-phenoxynonyl, 10-phenoxydecyl, 11-phenoxyundecyl,12-phenoxydodecyl, 13-phenoxytridecyl, 14-phenoxytetradecyl,15-phenoxypentadecyl, 16-phenoxyhexadecyl, 17-phenoxyheptadecyl,18-phenoxyoctadecyl, 19-phenoxynonadecyl and 20-phenoxyicosyl.

The phenoxyalkyl as a substituent at Rl, where the alkyl moiety has 2 to8 carbon atoms, is the aforementioned phenoxyalkyl having the specifiednumbers of carbon atoms.

The phenoxyalkoxy as a substituent at Rd, Re, Rf, Rg or Rk is that wherethe alkoxy moiety is a straight- or branched chain alkoxy having 1 to 20carbon atoms and is exemplified by phenoxymethoxy, 1-phenoxyethyloxy,2-phenoxyethyloxy, 1-phenoxypropyloxy, 2-phenoxypropyloxy,3-phenoxypropyloxy, 4-phenoxybutyloxy, 5-phenoxypentyloxy,6-phenoxyhexyloxy, 7-phenoxyheptyloxy, 8-phenoxyoctyloxy,9-phenoxynonyloxy, 10-phenoxydecyloxy, 11-phenoxyundecyloxy,12-phenoxydodecyloxy, 13-phenoxytridecyloxy, 14-phenoxytetradecyloxy,15-phenoxypentadecyloxy, 16-phenoxyhexadecyloxy,17-phenoxyheptadecyloxy, 18-phenoxyoctadecyloxy, 19-phenoxynonadecyloxyand 20-phenoxyicosyloxy.

The phenoxyalkoxy as a substituent at Rl, where the alkoxy moiety has 2to 8 carbon atoms, is the aforementioned phenoxyalkoxy having thespecified numbers of carbon atoms.

The alkyl at R², R² a, R² b, R² c, R³, R³ a, R³ b, R³ c, R⁴, R⁴ a, R⁴ b,R⁵, R⁵ a, R⁵ b or R⁶ is that having 1 to 20 carbon atoms and isexemplified by methyl, ethyl, propyl, isopropyl, butyl, isobutyl,tert-butyl, pentyl, isopentyl, tert-pentyl, hexyl, heptyl, octyl, nonyl,decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl,heptadecyl, octadecyl, nonadecyl and icosyl.

The aralkyl at R², R³, R⁴, R⁵ or R⁶ is that where the alkyl moiety is astraight- or branched chain alkyl having 1 to 20 carbon atoms and isexemplified by benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl,2-phenylpropyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl,6-phenylhexyl, 7-phenylheptyl, 8-phenyloctyl, 9-phenylnonyl,10-phenyldecyl, 11-phenylundecyl, 12-phenyldodecyl, 13-phenyltridecyl,14-phenyltetradecyl, 15-phenylpentadecyl, 16-phenylhexadecyl,17-phenylheptadecyl, 18-phenyloctadecyl, 19-phenylnonadecyl and20-phenylicosyl.

The acyl at R², R² a, R² b, R³, R³ a, R³ b, R⁴, R⁴ a, R⁴ b, R⁵, R⁵ a, R⁵b or R⁶ is optionally substituted alkanoyl or aroyl where the alkanoylis a straight- or branched chain alkanoyl having 1 to 20 carbon atoms,and alkoanoyl is exemplified by formyl, acetyl, propionyl, butyryl,isobutyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl,decanoyl, undecanoyl, dodecanoyl, tridecanoyl, tetradecanoyl,pentadecanoyl, hexadecanoyl, heptadecanoyl, octadecanoyl, nonadecanoyland icosanoyl, which may be substituted by phenyl. Examples thereofinclude phenylacetyl and phenylpropionyl. Examples of aroyl includebenzoyl.

The alkoxycarbonyl at R², R² a, R³, R³ a, R⁴, R⁴ a, R⁵, R⁵ a or R⁶ isthat where the alkoxy moiety is an optionally substituted straight- orbranched chain alkoxy having 1 to 20 carbon atoms and is exemplified bymethoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl,butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl,pentyloxycarbonyl, isopentyloxycarbonyl, tert-pentyloxycarbonyl,hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl,decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl,tridecyloxycarbonyl, tetradecyloxycarbonyl, pentadecyloxycarbonyl,hexadecyloxycarbonyl, heptadecyloxycarbonyl, octadecyloxycarbonyl,nonadecyloxycarbonyl and icosyloxycarbonyl, which may be substituted byphenyl. Examples thereof include benzyloxycarbonyl.

The alkylene chain formed by R⁴ and R⁵ is a straight- or branched chainalkylene having 1 to 5 carbon atoms and is exemplified by methylene,ethylene, trimethylene, propylene, butylene, 1,2-dimethylethylene andpentamethylene.

The alkyl as a substituent at R⁴ or R⁵ is a straight- or branched chainalkyl having 1 to 5 carbon atoms and is exemplified by methyl, ethyl,propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl and pentyl.

The aryl as a substituent at R⁴ or R⁵ is, for example, phenyl ornaphthyl.

The aralkyl as a substituent at R⁴ or R⁵ is that where the alkyl moietyis a straight- or branched chain alkyl having 1 to 5 carbon atoms and isexemplified by benzyl, 2-phenethyl, 1-phenylethyl, 1-phenylpropyl,2-phenylpropyl, 3-phenylpropyl, 4-phenylbutyl and 5-phenylpentyl.

The alkylene chain formed by R⁴ and R⁵, which is substituted by alkyl,aryl or aralkyl, is preferably ethylidene, isopropylidene, benzylideneor 2-phenylethylidene.

The preferable compounds of the present invention are shown in thefollowing tables.

    __________________________________________________________________________     ##STR32##                                                                    R.sup.1                  R.sup.2                                                                              R.sup.3                                                                            R.sup.4                                                                           R.sup.5                              __________________________________________________________________________    CH(CH.sub.3).sub.2       H      H    H   H                                    CH(CH.sub.3)C.sub.2 H.sub.5                                                                            H      H    H   H                                    CH(CH.sub.3)C.sub.3 H.sub.7                                                                            H      H    H   H                                    C(CH.sub.3).sub.3        H      H    H   H                                    C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                                      H      H    H   H                                    C(CH.sub.3)C.sub.3 H.sub.7                                                                             H      H    H   H                                    C.sub.5 H.sub.11         H      H    H   H                                    C.sub.5 H.sub.11         COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.6 H.sub.13         H      H    H   H                                    C.sub.7 H.sub.15         H      H    H   H                                    C.sub.7 H.sub.15         COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.8 H.sub.17         H      H    H   H                                    C.sub.9 H.sub.19         H      H    H   H                                    C.sub.9 H.sub.19         COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.10 H.sub.21        H      H    H   H                                    C.sub.11 H.sub.21        H      H    H   H                                    C.sub.11 H.sub.23        COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                            CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.2 !.sub.2 CH.sub.2 CH(CH.sub.3).sub.2    1                        H      H    H   H                                     CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.2 !.sub.2 CH.sub.2 CH(CH.sub.3).sub.2    2                        COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.12 H.sub.25        H      H    H   H                                    C.sub.12 H.sub.25        COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.13 H.sub.27        H      H    H   H                                    C.sub.13 H.sub.27        CH.sub.3                                                                             CH.sub.3                                                                           H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.10 H.sub.21                                                         H      H    H   H                                    C.sub.14 H.sub.29        H      H    H   H                                    C.sub.14 H.sub.29        COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.15 H.sub.31        H      H    H   H                                    C.sub.16 H.sub.33        H      H    H   H                                    C.sub.17 H.sub.35        H      H    H   H                                    C.sub.17 H.sub.35        C.sub.2 H.sub.5                                                                      H    H   H                                    C.sub.17 H.sub.35        H      H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.17 H.sub.35        COC.sub.4 H.sub.9                                                                    H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.17 H.sub.35        COC.sub.4 H.sub.9                                                                    H    H   H                                    C.sub.17 H.sub.35        C.sub.5 H.sub.11                                                                     H    H   H                                    C.sub.17 H.sub.35        COC.sub.9 H.sub.19                                                                   H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.17 H.sub.35        COC.sub.9 H.sub.19                                                                   H    H   H                                    C.sub.17 H.sub.35        C.sub.10 H.sub.21                                                                    H    H   H                                    C.sub.17 H.sub.35        CH.sub.3                                                                             CH.sub.3                                                                           COCH.sub.3                                                                        COCH.sub.3                           C.sub.17 H.sub.35        CH.sub.3                                                                             CH.sub.3                                                                           H   H                                    C.sub.18 H.sub.37        H      H    H   H                                    C.sub.19 H.sub.39        H      H    H   H                                    C.sub.20 H.sub.41        H      H    H   H                                    C.sub.21 H.sub.43        H      H    H   H                                    C.sub.22 H.sub.45        H      H    H   H                                    C.sub.23 H.sub.47        H      H    H   H                                    C.sub.24 H.sub.49        H      H    H   H                                    C.sub.25 H.sub.51        H      H    H   H                                    C.sub.26 H.sub.53        H      H    H   H                                    C.sub.27 H.sub.55        H      H    H   H                                    C.sub.28 H.sub.57        H      H    H   H                                    C.sub.29 H.sub.59        H      H    H   H                                    CHCH.sub.2               H      H    H   H                                    CHCHCH.sub.3             H      H    H   H                                    CHCHC.sub.2 H.sub.5      H      H    H   H                                    CHCHC.sub.3 H.sub.7      H      H    H   H                                    CHCHC.sub.4 H.sub.9      H      H    H   H                                    CHCHC.sub.5 H.sub.11     H      H    H   H                                    CHCHC.sub.6 H.sub.13     H      H    H   H                                    CHCHC.sub.7 H.sub.15     H      H    H   H                                    CHCHC.sub.9 H.sub.19     H      H    H   H                                    CHCHC.sub.11 H.sub.23    H      H    H   H                                    CHCHC.sub.13 H.sub.27    H      H    H   H                                    CHCHC.sub.15 H.sub.31    H      H    H   H                                    CHCHC.sub.17 H.sub.35    H      H    H   H                                    CHCHC.sub.27 H.sub.55    H      H    H   H                                    CH.sub.2 CHCH.sub.2      H      H    H   H                                    CH.sub.2 CHCHCH.sub.3    H      H    H   H                                    CH.sub.2 CHCHC.sub.2 H.sub.5                                                                           H      H    H   H                                    CH.sub.2 CHCHC.sub.3 H.sub.7                                                                           H      H    H   H                                    CH.sub.2 CHCHC.sub.4 H.sub.9                                                                           H      H    H   H                                    CH.sub.2 CHCHC.sub.5 H.sub.11                                                                          H      H    H   H                                    CH.sub.2 CHCHC.sub.6 H.sub.13                                                                          H      H    H   H                                    CH.sub.2 CHCHC.sub.8 H.sub.17                                                                          H      H    H   H                                    CH.sub.2 CHCHC.sub.10 H.sub.21                                                                         H      H    H   H                                    CH.sub.2 CHCHC.sub.12 H.sub.25                                                                         H      H    H   H                                    CH.sub.2 CHCHC.sub.14 H.sub.29                                                                         H      H    H   H                                    CH.sub.2 CHCHC.sub.16 H.sub.33                                                                         H      H    H   H                                    CH.sub.2 CHCHC.sub.26 H.sub.53                                                                         H      H    H   H                                    (CH.sub.2).sub.2 CHCH.sub.2                                                                            H      H    H   H                                    (CH.sub.2).sub.2 CHCHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.2 C(CH.sub.3)CHC.sub.4 H.sub.9                                                          H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.4 H.sub.9                                                                   H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.7 H.sub.15                                                                  H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.9 H.sub.19                                                                  H      H    H   H                                    trans: (CH.sub.2).sub.2 CHCHC.sub.9 H.sub.19                                                           H      H    H   H                                    cis: (CH.sub.2).sub.2 CHCHC.sub.9 H.sub.19                                                             H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.11 H.sub.23                                                                 H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.13 H.sub.27                                                                 H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.15 H.sub.31                                                                 H      H    H   H                                    (CH.sub.2).sub.2 CHCHC.sub.25 H.sub.51                                                                 H      H    H   H                                    (CH.sub.2).sub.3 CHCH.sub.2                                                                            H      H    H   H                                    (CH.sub.2).sub.3 CHCHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.3 C(CH.sub.3)CHC.sub.3 H.sub.7                                                          H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.4 H.sub.9                                                                   H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.6 H.sub.13                                                                  H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.8 H.sub.17                                                                  H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.12 H.sub.25                                                                 H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.14 H.sub.29                                                                 H      H    H   H                                    (CH.sub.2).sub.3 CHCHC.sub.24 H.sub.49                                                                 H      H    H   H                                    (CH.sub.2).sub.4 CHCH.sub.2                                                                            H      H    H   H                                    (CH.sub.2).sub.4 CHCHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.4 CHCHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.4 CHCHC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.4 CHCHC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.4 CHCHC.sub.7 H.sub.15                                                                  H      H    H   H                                    (CH.sub.2).sub.4 CHCHC.sub.9 H.sub.19                                                                  H      H    H   H                                    (CH.sub.2).sub.4 CHCHC.sub.11 H.sub.23                                                                 H      H    H   H                                    (CH.sub.2).sub.4 CHCHC.sub.13 H.sub.27                                                                 H      H    H   H                                    (CH.sub.2).sub.4 CHCHC.sub.23 H.sub.47                                                                 H      H    H   H                                    (CH.sub.2).sub.5 CHCH.sub.2                                                                            H      H    H   H                                    (CH.sub.2).sub.5 CHCHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.5 CHCHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.5 CHCHC.sub.4 H.sub.9                                                                   H      H    H   H                                    (CH.sub.2).sub.5 CHCHC.sub.6 H.sub.13                                                                  H      H    H   H                                    (CH.sub.2).sub.5 CHCHC.sub.8 H.sub.17                                                                  H      H    H   H                                    (CH.sub.2).sub.5 CHCHC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.5 CHCHC.sub.12 H.sub.25                                                                 H      H    H   H                                    (CH.sub.2).sub.5 CHCHC.sub.22 H.sub.45                                                                 H      H    H   H                                    (CH.sub.2).sub.6 CHCH.sub.2                                                                            H      H    H   H                                    (CH.sub.2).sub.6 CHCHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.6 CHCHC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.6 CHCHC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.6 CHCHC.sub.7 H.sub.15                                                                  H      H    H   H                                    (CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)(CH.sub.2).sub.3 CHCHC.sub.9 H.sub.19                              H      H    H   H                                    (CH.sub.2).sub.6 CHCHC.sub.9 H.sub.19                                                                  H      H    H   H                                    (CH.sub.2).sub.6 CHCHC.sub.11 H.sub.23                                                                 H      H    H   H                                    (CH.sub.2).sub.6 CHCHC.sub.21 H.sub.43                                                                 H      H    H   H                                    (CH.sub.2).sub.7 CHCH.sub.2                                                                            H      H    H   H                                    (CH.sub.2).sub.7 CHCHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.7 CHCHC.sub.4 H.sub.9                                                                   H      H    H   H                                    (CH.sub.2).sub.7 CHCHC.sub.6 H.sub.13                                                                  H      H    H   H                                    (CH.sub.2).sub.7 CHCHC.sub.8 H.sub.17                                                                  H      H    H   H                                    (CH.sub.2).sub.7 CHCHC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.7 CHCHC.sub.20 H.sub.41                                                                 H      H    H   H                                    (CH.sub.2).sub.8 CHCHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.8 CHCHC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.8 CHCHC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.8 CHCHC.sub.7 H.sub.15                                                                  H      H    H   H                                    (CH.sub.2).sub.8 CHCHC.sub.9 H.sub.19                                                                  H      H    H   H                                    (CH.sub.2).sub.8 CHCHC.sub.19 H.sub.39                                                                 H      H    H   H                                    (CH.sub.2).sub.10 CHCHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.10 CHCHC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.3 CH(C.sub.3 H.sub.7)(CH.sub.2).sub.6 CHCHC.sub.5 H.sub.11                              H      H    H   H                                    (CH.sub.2).sub.10 CHCHC.sub.5 H.sub.11                                                                 H      H    H   H                                    (CH.sub.2).sub.10 CHCHC.sub.7 H.sub.15                                                                 H      H    H   H                                    (CH.sub.2).sub.10 CHCHC.sub.17 H.sub.35                                                                H      H    H   H                                    (CH.sub.2).sub.12 CHCHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.12 CHCHC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.12 CHCHC.sub.5 H.sub.11                                                                 H      H    H   H                                    (CH.sub.2).sub.12 CHCHC.sub.15 H.sub.31                                                                H      H    H   H                                    (CH.sub.2).sub.14 CHCHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.14 C(CH.sub.3)CHC.sub.3 H.sub.7                                                         H      H    H   H                                    (CH.sub.2).sub.14 CHCHC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.14 CHCHC.sub.13 H.sub.27                                                                H      H    H   H                                    (CH.sub.2).sub.16 CHCHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.16 CHCHC.sub.11 H.sub.23                                                                H      H    H   H                                    (CH.sub.2).sub.19 CHCHC.sub.8 H.sub.17                                                                 H      H    H   H                                    (CH.sub.2).sub.20 CHCHC.sub.7 H.sub.15                                                                 H      H    H   H                                    (CH.sub.2).sub.22 CHCHC.sub.5 H.sub.11                                                                 H      H    H   H                                    (CH.sub.2).sub.24 CHCHC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.26 CHCHCH.sub.3                                                                         H      H    H   H                                     CHC(CH.sub.3)CH.sub.2 CH.sub.2 !.sub.3 H                                                              H      H    H   H                                     CHC(CH.sub.3)CH.sub.2 CH.sub.2 !.sub.3 H                                                              COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C CH                     H      H    H   H                                    C CCH.sub.3              H      H    H   H                                    C CC.sub.2 H.sub.5       H      H    H   H                                    C CC.sub.3 H.sub.7       H      H    H   H                                    C CC.sub.4 H.sub.9       H      H    H   H                                    C CC.sub.5 H.sub.11      H      H    H   H                                    C CC.sub.6 H.sub.13      H      H    H   H                                    C CC.sub.7 H.sub.15      H      H    H   H                                    C CC.sub.9 H.sub.19      H      H    H   H                                    C CC.sub.11 H.sub.23     H      H    H   H                                    C CC.sub.12 H.sub.25     H      H    H   H                                    C CC.sub.12 H.sub.25     COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C CC.sub.13 H.sub.27     H      H    H   H                                    C CC.sub.15 H.sub.31     H      H    H   H                                    C CC.sub.17 H.sub.35     H      H    H   H                                    C CC.sub.27 H.sub.55     H      H    H   H                                    CH.sub.2 C CH            H      H    H   H                                    CH.sub.2 C CCH.sub.3     H      H    H   H                                    CH.sub.2 C CC.sub.2 H.sub.5                                                                            H      H    H   H                                    CH.sub.2 C CC.sub.3 H.sub.7                                                                            H      H    H   H                                    CH.sub.2 C CC.sub.4 H.sub.9                                                                            H      H    H   H                                    CH.sub.2 C CC.sub.5 H.sub.11                                                                           H      H    H   H                                    CH.sub.2 C CC.sub.6 H.sub.13                                                                           H      H    H   H                                    CH.sub.2 C CC.sub.8 H.sub.17                                                                           H      H    H   H                                    CH.sub.2 C CC.sub.10 H.sub.21                                                                          H      H    H   H                                    CH.sub.2 C CC.sub.12 H.sub.25                                                                          H      H    H   H                                    CH.sub.2 C CC.sub.14 H.sub.29                                                                          H      H    H   H                                    CH.sub.2 C CC.sub.16 H.sub.33                                                                          H      H    H   H                                    CH.sub.2 C CC.sub.26 H.sub.53                                                                          H      H    H   H                                    (CH.sub.2).sub.2 C CH    H      H    H   H                                    (CH.sub.2).sub.2 C CCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.4 H.sub.9                                                                    H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.5 H.sub.11                                                                   H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.7 H.sub.15                                                                   H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.9 H.sub.19                                                                   H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.11 H.sub.23                                                                  H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.13 H.sub.27                                                                  H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.15 H.sub.31                                                                  H      H    H   H                                    (CH.sub.2).sub.2 C CC.sub.25 H.sub.51                                                                  H      H    H   H                                    (CH.sub.2).sub.3 C CH    H      H    H   H                                    (CH.sub.2).sub.3 C CCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.4 H.sub.9                                                                    H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.6 H.sub.13                                                                   H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.8 H.sub.17                                                                   H      H    H   H                                    (CH.sub.2).sub.2 CH(CH.sub.3)C CC.sub.10 H.sub.21                                                      H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.12 H.sub.25                                                                  H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.14 H.sub.29                                                                  H      H    H   H                                    (CH.sub.2).sub.3 C CC.sub.24 H.sub.49                                                                  H      H    H   H                                    (CH.sub.2).sub.4 C CH    H      H    H   H                                    (CH.sub.2).sub.4 C CCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.4 C CC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.4 C CC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.4 C CC.sub.5 H.sub.11                                                                   H      H    H   H                                    (CH.sub.2).sub.4 C CC.sub.7 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.4 C CC.sub.9 H.sub.19                                                                   H      H    H   H                                    (CH.sub.2).sub.4 C CC.sub.11 H.sub.23                                                                  H      H    H   H                                    (CH.sub.2).sub.4 C CC.sub.13 H.sub.27                                                                  H      H    H   H                                    (CH.sub.2).sub.4 C CC.sub.23 H.sub.47                                                                  H      H    H   H                                    (CH.sub.2).sub.5 C CH    H      H    H   H                                    (CH.sub.2).sub.5 C CCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.5 C CC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.5 C CC.sub.4 H.sub.9                                                                    H      H    H   H                                    (CH.sub.2).sub.5 C CC.sub.6 H.sub.13                                                                   H      H    H   H                                    (CH.sub.2).sub.5 C CC.sub.8 H.sub.17                                                                   H      H    H   H                                    (CH.sub.2).sub.5 C CC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.5 C CC.sub.12 H.sub.25                                                                  H      H    H   H                                    (CH.sub.2).sub.5 C CC.sub.22 H.sub.45                                                                  H      H    H   H                                    (CH.sub.2).sub.6 C CH    H      H    H   H                                    (CH.sub.2).sub.6 C CCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.6 C CC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.6 C CC.sub.5 H.sub.11                                                                   H      H    H   H                                    (CH.sub.2).sub.6 C CC.sub.7 H.sub.15                                                                   H      H    H   H                                    (CH.sub.2).sub.6 C CC.sub.9 H.sub.19                                                                   H      H    H   H                                    (CH.sub.2).sub.6 C CC.sub.11 H.sub.23                                                                  H      H    H   H                                    (CH.sub.2).sub.6 C CC.sub.21 H.sub.43                                                                  H      H    H   H                                    (CH.sub.2).sub.7 C CH    H      H    H   H                                    (CH.sub.2).sub.7 C CC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.7 C CC.sub.4 H.sub.9                                                                    H      H    H   H                                    (CH.sub.2).sub.7 C CC.sub.6 H.sub.13                                                                   H      H    H   H                                    (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.4 C CC.sub.8 H.sub.17                                      H      H    H   H                                    (CH.sub.2).sub.7 C CC.sub.8 H.sub.17                                                                   H      H    H   H                                    (CH.sub.2).sub.7 C CC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.7 C CC.sub.20 H.sub.41                                                                  H      H    H   H                                    (CH.sub.2).sub.8 C CCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.8 C CC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.8 C CC.sub.5 H.sub.11                                                                   H      H    H   H                                    (CH.sub.2).sub.8 C CC.sub.7 H.sub.15                                                                   H      H    H   H                                    (CH.sub.2).sub.8 C CC.sub.9 H.sub.19                                                                   H      H    H   H                                    (CH.sub.2).sub.8 C CC.sub.19 H.sub.39                                                                  H      H    H   H                                    (CH.sub.2).sub.10 C CCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.10 C CC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.10 C CC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)(CH.sub.2).sub.6 C CC.sub.7 H.sub.15                                      H      H    H   H                                    (CH.sub.2).sub.10 C CC.sub.7 H.sub.15                                                                  H      H    H   H                                    (CH.sub.2).sub.10 C CC.sub.17 H.sub.35                                                                 H      H    H   H                                    (CH.sub.2).sub.12 C CCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.12 C CC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.12 C CC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.12 C CC.sub.15 H.sub.31                                                                 H      H    H   H                                    (CH.sub.2).sub.14 C CCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.14 C CC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.14 C CC.sub.13 H.sub.27                                                                 H      H    H   H                                    (CH.sub.2).sub.16 C CCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.16 C CC.sub.11 H.sub.23                                                                 H      H    H   H                                    (CH.sub.2).sub.18 C CC.sub.9 H.sub.19                                                                  H      H    H   H                                    (CH.sub.2).sub.20 C CC.sub.7 H.sub.15                                                                  H      H    H   H                                    (CH.sub.2).sub.22 C CC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.24 C CC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.26 C CCH.sub.3                                                                          H      H    H   H                                    CH.sub.2 OH              H      H    H   H                                    (CH.sub.2).sub.2 OH      H      H    H   H                                    CH.sub.2 (OH)CH.sub.3    H      H    H   H                                    (CH.sub.2).sub.3 OH      H      H    H   H                                    (CH.sub.2).sub.4 OH      H      H    H   H                                    (CH.sub.2).sub.5 OH      H      H    H   H                                    (CH.sub.2).sub.6 OH      H      H    H   H                                    (CH.sub.2).sub.7 OH      H      H    H   H                                    (CH.sub.2).sub.8 OH      H      H    H   H                                    (CH.sub.2).sub.9 OH      H      H    H   H                                    (CH.sub.2).sub.10 OH     H      H    H   H                                    (CH.sub.2).sub.11 OH     H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.6 H.sub.13)OH                                                                H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.6 H.sub.13)OH                                                                COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.17 OH     H      H    H   H                                    (CH.sub.2).sub.19 OH     H      H    H   H                                    (CH.sub.2).sub.29 OH     H      H    H   H                                    COOH                     H      H    H   H                                    CH.sub.2 COOH            H      H    H   H                                    (CH.sub.2).sub.2 COOH    H      H    H   H                                    (CH.sub.2).sub.3 COOH    H      H    H   H                                    (CH.sub.2).sub.4 COOH    H      H    H   H                                    (CH.sub.2).sub.5 COOH    H      H    H   H                                    (CH.sub.2).sub.6 COOH    H      H    H   H                                    (CH.sub.2).sub.7 COOH    H      H    H   H                                    (CH.sub.2).sub.8 COOH    H      H    H   H                                    (CH.sub.2).sub.9 COOH    H      H    H   H                                    (CH.sub.2).sub.10 COOH   H      H    H   H                                    (CH.sub.2).sub.11 COOH   H      H    H   H                                    (CH.sub.2).sub.17 COOH   H      H    H   H                                    (CH.sub.2).sub.19 COOH   H      H    H   H                                    (CH.sub.2).sub.29 COOH   H      H    H   H                                    CH.sub.2 COOCH.sub.3     H      H    H   H                                    CH.sub.2 COOC.sub.2 H.sub.5                                                                            H      H    H   H                                    CH.sub.2 COOC.sub.10 H.sub.21                                                                          H      H    H   H                                    CH.sub.2 COOC.sub.14 H.sub.29                                                                          H      H    H   H                                    (CH.sub.2).sub.2 COOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.2 COOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.2 COOC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.2 COOC.sub.13 H.sub.27                                                                  H      H    H   H                                    (CH.sub.2).sub.3 COOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.3 COOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.3 CCOC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.3 COOC.sub.12 H.sub.25                                                                  H      H    H   H                                    (CH.sub.2).sub.4 COOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.4 COOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.4 COOC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.4 COOC.sub.11 H.sub.23                                                                  H      H    H   H                                    (CH.sub.2).sub.5 COOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.5 COOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.5 COOC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.6 COOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.6 COOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.6 COOC.sub.9 H.sub.19                                                                   H      H    H   H                                    (CH.sub.2).sub.7 COOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.7 COOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.7 COOC.sub.8 H.sub.17                                                                   H      H    H   H                                    (CH.sub.2).sub.8 COOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.3 CH(C.sub.4 H.sub.9)COOC.sub.2 H.sub.5                                                 H      H    H   H                                    (CH.sub.2).sub.8 COOC.sub.7 H.sub.15                                                                   H      H    H   H                                    (CH.sub.2).sub.9 COOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.9 COOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.9 COOC.sub.6 H.sub.13                                                                   H      H    H   H                                    (CH.sub.2).sub.10 COOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.10 COOCH.sub.3                                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.10 COOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.10 COOC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.11 COOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.11 COOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.11 COOC.sub.4 H.sub.9                                                                   H      H    H   H                                    (CH.sub.2).sub.17 COOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.17 COOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.17 CCOC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.19 COOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.19 COOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.19 COOC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.29 COOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.29 COOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.29 COOC.sub.10 H.sub.21                                                                 H      H    H   H                                    CH.sub.2 OCOCH.sub.3     H      H    H   H                                    CH.sub.2 OCOC.sub.2 H.sub.5                                                                            H      H    H   H                                    CH.sub.2 OCOC.sub.3 H.sub.7                                                                            H      H    H   H                                    CH.sub.2 OCOC.sub.14 H.sub.29                                                                          H      H    H   H                                    (CH.sub.2).sub.2 OCOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.2 OCOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.2 OCOC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.2 OCOC.sub.13 H.sub.27                                                                  H      H    H   H                                    (CH.sub.2).sub.3 OCOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.3 OCOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.3 OCOC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.3 OCOC.sub.12 H.sub.25                                                                  H      H    H   H                                    (CH.sub.2).sub.4 OCOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.4 OCOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.4 OCOC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.4 OCOC.sub.11 H.sub.23                                                                  H      H    H   H                                    (CH.sub.2).sub.5 OCOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.5 OCOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.5 OCOC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.5 OCOC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.6 OCOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.6 OCOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.6 OCOC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.6 OCOC.sub.9 H.sub.19                                                                   H      H    H   H                                    (CH.sub.2).sub.7 OCOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.7 OCOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.7 OCOC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.7 OCOC.sub.8 H.sub.17                                                                   H      H    H   H                                    (CH.sub.2).sub.8 OCOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.8 OCOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.8 OCOC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.8 OCOC.sub.7 H.sub.15                                                                   H      H    H   H                                    (CH.sub.2).sub.9 OCOCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.9 OCOC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.2 CH(C.sub.6 H.sub.13)OCOC.sub.3 H.sub.7                                                H      H    H   H                                    (CH.sub.2).sub.9 OCOC.sub.6 H.sub.13                                                                   H      H    H   H                                    (CH.sub.2).sub.10 OCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.10 OCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.10 OCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.10 OCOC.sub.5 H.sub.11                                                                  H      H    H   H                                    (CH.sub.2).sub.11 OCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.11 OCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.11 OCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.11 OCOC.sub.4 H.sub.9                                                                   H      H    H   H                                    (CH.sub.2).sub.17 OCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.17 OCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.17 OCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.17 OCOC.sub.9 H.sub.19                                                                  H      H    H   H                                    (CH.sub.2).sub.19 OCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.19 OCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.19 OCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.19 CCOC.sub.9 H.sub.19                                                                  H      H    H   H                                    (CH.sub.2).sub.29 CCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.29 OCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.29 OCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.29 OCOC.sub.9 H.sub.19                                                                  H      H    H   H                                    CH(CH.sub.3)OCOCH.sub.3  H      H    H   H                                    CH(CH.sub.3)OCOC.sub.2 H.sub.5                                                                         H      H    H   H                                    CH(CH.sub.3)OCOC.sub.3 H.sub.7                                                                         H      H    H   H                                    CH(CH.sub.3)OCOC.sub.14 H.sub.29                                                                       H      H    H   H                                    CH.sub.2 COC.sub.7 H.sub.15                                                                            H      H    H   H                                    CH.sub.2 COC.sub.9 H.sub.19                                                                            H      H    H   H                                    CH.sub.2 COC.sub.11 H.sub.23                                                                           H      H    H   H                                    (CH.sub.2).sub.6 COC.sub.6 H.sub.13                                                                    H      H    H   H                                    (CH.sub.2).sub.6 COC.sub.6 H.sub.13                                                                    COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 COC.sub.15 H.sub.31                                                                           H      H    H   H                                    CH.sub.2 COC.sub.17 H.sub.35                                                                           H      H    H   H                                    (CH.sub.2).sub.2 SC.sub.12 H.sub.25                                                                    H      H    H   H                                    (CH.sub.2).sub.2 SC.sub.12 H.sub.25                                                                    COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 CH(C.sub.7 H.sub.15)SCH.sub.3                                                                 H      H    H   H                                    CH.sub.2 CH(C.sub.7 H.sub.15)SC.sub.2 H.sub.5                                                          H      H    H   H                                    CH.sub.2 CH(C.sub.7 H.sub.15)SC.sub.7 H.sub.15                                                         H      H    H   H                                    (CH.sub.2).sub.9 SCH.sub.3                                                                             H      H    H   H                                    (CH.sub.2).sub.9 SC.sub.2 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.9 SC.sub.7 H.sub.15                                                                     H      H    H   H                                    CH.sub.2 CH(C.sub.9 H.sub.19)SCH.sub.3                                                                 H      H    H   H                                    CH.sub.2 CH(C.sub.9 H.sub.19)SC.sub.2 H.sub.5                                                          H      H    H   H                                    CH.sub.2 CH(C.sub.9 H.sub.19)SC.sub.7 H.sub.15                                                         H      H    H   H                                    (CH.sub.2).sub.11 SCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.11 SC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.11 SC.sub.7 H.sub.15                                                                    H      H    H   H                                    CH.sub.2 CH(C.sub.11 H.sub.23)SCH.sub.3                                                                H      H    H   H                                    CH.sub.2 CH(C.sub.11 H.sub.23)SC.sub.2 H.sub.5                                                         H      H    H   H                                    CH.sub.2 CH(C.sub.11 H.sub.23)SC.sub.3 H.sub.7                                                         H      H    H   H                                    (CH.sub.2).sub.13 SCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.13 SC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.13 SC.sub.7 H.sub.15                                                                    H      H    H   H                                    CH.sub.2 CH(C.sub.15 H.sub.31)SCH.sub.3                                                                H      H    H   H                                    CH.sub.2 CH(C.sub.15 H.sub.31)SC.sub.2 H.sub.5                                                         H      H    H   H                                    CH.sub.2 CH(C.sub.15 H.sub.31)SC.sub.10 H.sub.21                                                       H      H    H   H                                    CH.sub.2 CH(C.sub.17 H.sub.35)SCH.sub.3                                                                H      H    H   H                                    CH.sub.2 CH(C.sub.17 H.sub.35)SC.sub.2 H.sub.5                                                         H      H    H   H                                    CH.sub.2 CH(C.sub.17 H.sub.35)SC.sub.10 H.sub.21                                                       H      H    H   H                                    CH.sub.2 NH.sub.2        H      H    H   H                                    (CH.sub.2).sub.2 NH.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.3 NH.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.4 NH.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.5 NH.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.6 NH.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.3 CH(C.sub.3 H.sub.7)NH.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.8 NH.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.9 NH.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.10 NH.sub.2                                                                             H      H    H   H                                    (CH.sub.2).sub.11 NH.sub.2                                                                             H      H    H   H                                    (CH.sub.2).sub.17 NH.sub.2                                                                             H      H    H   H                                    (CH.sub.2).sub.19 NH.sub.2                                                                             H      H    H   H                                    (CH.sub.2).sub.29 NH.sub.2                                                                             H      H    H   H                                    CH.sub.2 NHCOOCH.sub.3   H      H    H   H                                    CH.sub.2 NHCOOC.sub.2 H.sub.5                                                                          H      H    H   H                                    CH.sub.2 NHCOOC.sub.10 H.sub.21                                                                        H      H    H   H                                    CH.sub.2 NHCOOC.sub.14 H.sub.29                                                                        H      H    H   H                                    (CH.sub.2).sub.2 NHCOOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.2 NHCOOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.2 NHCOOC.sub.10 H.sub.21                                                                H      H    H   H                                    (CH.sub.2).sub.2 NHCOOC.sub.13 H.sub.27                                                                H      H    H   H                                    (CH.sub.2).sub.3 NHCOOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.3 NHCOOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.3 NHCOOC.sub.10 H.sub.21                                                                H      H    H   H                                    (CH.sub.2).sub.3 NHCOOC.sub.12 H.sub.25                                                                H      H    H   H                                    (CH.sub.2).sub.4 NHCCOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.4 NHCOOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.4 NHCOOC.sub.10 H.sub.21                                                                H      H    H   H                                    (CH.sub.2).sub.4 NHCOOC.sub.11 H.sub.23                                                                H      H    H   H                                    (CH.sub.2).sub.5 NHCOOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.5 NHCOOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.5 NHCOOC.sub.10 H.sub.21                                                                H      H    H   H                                    (CH.sub.2).sub.6 NHCOOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.6 NHCOOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.6 NHCOOC.sub.9 H.sub.19                                                                 H      H    H   H                                    (CH.sub.2).sub.7 NHCOOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.7 NHCOOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.7 NHCOOC.sub.8 H.sub.17                                                                 H      H    H   H                                    (CH.sub.2).sub.8 NHCOOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.8 NHCOOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.8 NHCOOC.sub.7 H.sub.15                                                                 H      H    H   H                                    (CH.sub.2).sub.9 NHCOOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.9 NHCOOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.9 NHCOOC.sub.6 H.sub.13                                                                 H      H    H   H                                    (CH.sub.2).sub.10 NHCOOCH.sub.3                                                                        H      H    H   H                                    (CH.sub.2).sub.10 NHCOOC.sub.2 H.sub.5                                                                 H      H    H   H                                    (CH.sub.2).sub.10 NHCOOC.sub.5 H.sub.11                                                                H      H    H   H                                    (CH.sub.2).sub.11 NHCOOCH.sub.3                                                                        H      H    H   H                                    (CH.sub.2).sub.11 NHCOOC.sub.2 H.sub.5                                                                 H      H    H   H                                    (CH.sub.2).sub.11 NHCOOC.sub.4 H.sub.9                                                                 H      H    H   H                                    (CH.sub.2).sub.17 NHCOOCH.sub.3                                                                        H      H    H   H                                    (CH.sub.2).sub.17 NHCOOC.sub.2 H.sub.5                                                                 H      H    H   H                                    (CH.sub.2).sub.17 NHCOOC.sub.10 H.sub.21                                                               H      H    H   H                                    (CH.sub.2).sub.18 CH(C.sub.10 H.sub.21)NHCOOCH.sub.3                                                   H      H    H   H                                    (CH.sub.2).sub.19 NHCOOC.sub.2 H.sub.5                                                                 H      H    H   H                                    (CH.sub.2).sub.19 NHCOOC.sub.10 H.sub.21                                                               H      H    H   H                                    (CH.sub.2).sub.29 NHCOOCH.sub.3                                                                        H      H    H   H                                    (CH.sub.2).sub.29 NHCOOC.sub.2 H.sub.5                                                                 H      H    H   H                                    (CH.sub.2).sub.29 NHCOOC.sub.10 H.sub.21                                                               H      H    H   H                                    CH.sub.2 NHCOCH.sub.3    H      H    H   H                                    CH.sub.2 NHCOC.sub.2 H.sub.5                                                                           H      H    H   H                                    CH.sub.2 NHCOC.sub.3 H.sub.7                                                                           H      H    H   H                                    CH.sub.2 NHCOC.sub.11 H.sub.23                                                                         H      H    H   H                                    CH.sub.2 NHCOC.sub.14 H.sub.29                                                                         H      H    H   H                                    (CH.sub.2).sub.2 NHCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.2 NHCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.2 NHCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.2 NHCOC.sub.13 H.sub.27                                                                 H      H    H   H                                    (CH.sub.2).sub.3 NHCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.3 NHCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.3 NHCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.3 NHCOC.sub.12 H.sub.25                                                                 H      H    H   H                                    (CH.sub.2).sub.4 NHCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.4 NHCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.4 NHCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.4 NHCOC.sub.11 H.sub.23                                                                 H      H    H   H                                    (CH.sub.2).sub.5 NHCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.5 NHCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.5 NHCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.5 NHCOC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.6 NHCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.6 NHCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.6 NHCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.6 NHCOC.sub.9 H.sub.19                                                                  H      H    H   H                                    (CH.sub.2).sub.7 NHCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.7 NHCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.7 NHCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.7 NHCOC.sub.8 H.sub.17                                                                  H      H    H   H                                    (CH.sub.2).sub.8 NHCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.8 NHCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.8 NHCOC.sub.3 H.sub.7                                                                   H      H    H   H                                    (CH.sub.2).sub.8 NHCOC.sub.7 H.sub.15                                                                  H      H    H   H                                    (CH.sub.2).sub.9 NHCOCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.9 NHCOC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.4 CH(C.sub.4 H.sub.9)NHCOC.sub.3 H.sub.7                                                H      H    H   H                                    (CH.sub.2).sub.9 NHCOC.sub.6 H.sub.13                                                                  H      H    H   H                                    (CH.sub.2).sub.10 NHCOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.10 NHCOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.10 NHCOC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.10 NHCOC.sub.5 H.sub.11                                                                 H      H    H   H                                    (CH.sub.2).sub.11 NHCOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.11 NHCOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.11 NHCOC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.11 NHCOC.sub.4 H.sub.9                                                                  H      H    H   H                                    (CH.sub.2).sub.17 NHCOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.17 NHCOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.17 NHCOC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.17 NHCOC.sub.9 H.sub.19                                                                 H      H    H   H                                    (CH.sub.2).sub.19 NHCOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.19 NHCOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.19 NHCOC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.19 NHCOC.sub.9 H.sub.19                                                                 H      H    H   H                                    (CH.sub.2).sub.29 NHCOCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.29 NHCOC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.29 NHCOC.sub.3 H.sub.7                                                                  H      H    H   H                                    (CH.sub.2).sub.29 NHCOC.sub.9 H.sub.19                                                                 H      H    H   H                                    CH(CH.sub.3)NHCOCH.sub.3 H      H    H   H                                    CH(CH.sub.3)NHCOC.sub.2 H.sub.5                                                                        H      H    H   H                                    CH(CH.sub.3)NHCOC.sub.3 H.sub.7                                                                        H      H    H   H                                    CH(CH.sub.3)NHCOC.sub.14 H.sub.29                                                                      H      H    H   H                                    CH.sub.2 NHCH.sub.3      H      H    H   H                                    CH.sub.2 NHC.sub.2 H.sub.5                                                                             H      H    H   H                                    CH.sub.2 NHC.sub.3 H.sub.7                                                                             H      H    H   H                                    CH.sub.2 NHC.sub.12 H.sub.25                                                                           H      H    H   H                                    CH.sub.2 NHC.sub.15 H.sub.31                                                                           H      H    H   H                                    (CH.sub.2).sub.2 NHCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.2 NHC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.2 NHC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.2 NHC.sub.14 H.sub.29                                                                   H      H    H   H                                    (CH.sub.2).sub.3 NHCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.3 NHC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.3 NHC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.3 NHC.sub.13 H.sub.27                                                                   H      H    H   H                                    (CH.sub.2).sub.4 NHCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.4 NHC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.4 NHC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.4 NHC.sub.12 H.sub.25                                                                   H      H    H   H                                    (CH.sub.2).sub.5 NHCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.5 NHC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.5 NHC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.5 NHC.sub.11 H.sub.23                                                                   H      H    H   H                                    (CH.sub.2).sub.6 NHCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.6 NHC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.6 NHC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.6 NHC.sub.10 H.sub.21                                                                   H      H    H   H                                    (CH.sub.2).sub.7 NHCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.7 NHC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.7 NHC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.7 NHC.sub.9 H.sub.19                                                                    H      H    H   H                                    (CH.sub.2).sub.8 NHCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.8 NHC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.8 NHC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.8 NHC.sub.8 H.sub.17                                                                    H      H    H   H                                    (CH.sub.2).sub.9 NHCH.sub.3                                                                            H      H    H   H                                    (CH.sub.2).sub.9 NHC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.9 NHC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.9 NHC.sub.7 H.sub.15                                                                    H      H    H   H                                    (CH.sub.2).sub.10 NHCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.10 NHC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.10 NHC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.10 NHC.sub.6 H.sub.13                                                                   H      H    H   H                                    (CH.sub.2).sub.11 NHCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.11 NHC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.11 NHC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.4 CH(C.sub.6 H.sub.13)NHC.sub.5 H.sub.11                                                H      H    H   H                                    (CH.sub.2).sub.17 NHCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.17 NHC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.17 NHC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.17 NHC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.19 NHCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.19 NHC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.19 NHC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.19 NHC.sub.10 H.sub.21                                                                  H      H    H   H                                    (CH.sub.2).sub.29 NHCH.sub.3                                                                           H      H    H   H                                    (CH.sub.2).sub.29 NHC.sub.2 H.sub.5                                                                    H      H    H   H                                    (CH.sub.2).sub.29 NHC.sub.3 H.sub.7                                                                    H      H    H   H                                    (CH.sub.2).sub.29 NHC.sub.10 H.sub.21                                                                  H      H    H   H                                    CONHCH.sub.3             H      H    H   H                                    CONHC.sub.2 H.sub.5      H      H    H   H                                    CONHC.sub.10 H.sub.21    H      H    H   H                                    COOC.sub.15 H.sub.31     H      H    H   H                                    CH.sub.2 CONHCH.sub.3    H      H    H   H                                    CH.sub.2 CONHC.sub.2 H.sub.5                                                                           H      H    H   H                                    CH.sub.2 CONHC.sub.10 H.sub.21                                                                         H      H    H   H                                    CH.sub.2 CONHC.sub.14 H.sub.29                                                                         H      H    H   H                                    (CH.sub.2).sub.3 CONHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.3 CONHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.3 CONHC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.3 CONHC.sub.12 H.sub.25                                                                 H      H    H   H                                    (CH.sub.2).sub.4 CONHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.4 CONHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.4 CONHC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.4 CONHC.sub.11 H.sub.23                                                                 H      H    H   H                                    (CH.sub.2).sub.5 CONHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.5 CONHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.5 CONHC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.6 CONHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.6 CONHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.6 CONHC.sub.10 H.sub.21                                                                 H      H    H   H                                    (CH.sub.2).sub.7 CONHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.7 CONHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.7 CONHC.sub.8 H.sub.17                                                                  H      H    H   H                                    (CH.sub.2).sub.8 CONHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.8 CONHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.8 CONHC.sub.7 H.sub.15                                                                  H      H    H   H                                    (CH.sub.2).sub.9 CONHCH.sub.3                                                                          H      H    H   H                                    (CH.sub.2).sub.9 CONHC.sub.2 H.sub.5                                                                   H      H    H   H                                    (CH.sub.2).sub.9 CONHC.sub.6 H.sub.13                                                                  H      H    H   H                                    (CH.sub.2).sub.10 CONHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.10 CONHC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.10 CONHC.sub.5 H.sub.11                                                                 H      H    H   H                                    (CH.sub.2).sub.11 CONHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.11 CONHC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.11 CONHC.sub.4 H.sub.9                                                                  H      H    H   H                                    (CH.sub.2).sub.17 CONHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.8 CH(C.sub.8 H.sub.17)CONHC.sub.2 H.sub.5                                               H      H    H   H                                    (CH.sub.2).sub.17 CONHC.sub.10 H.sub.21                                                                H      H    H   H                                    (CH.sub.2).sub.19 CONHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.19 CONHC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.19 CONHC.sub.10 H.sub.21                                                                H      H    H   H                                    (CH.sub.2).sub.29 CONHCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.29 CONHC.sub.2 H.sub.5                                                                  H      H    H   H                                    (CH.sub.2).sub.29 CONHC.sub.10 H.sub.21                                                                H      H    H   H                                    CH.sub.2 NO.sub.2        H      H    H   H                                    (CH.sub.2).sub.2 NO.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.3 NO.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.4 NO.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.5 NO.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.6 NO.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.7 NO.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.8 NO.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.9 NO.sub.2                                                                              H      H    H   H                                    (CH.sub.2).sub.10 NO.sub.2                                                                             H      H    H   H                                    (CH.sub.2).sub.4 CH(C.sub.6 H.sub.13)NO.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.17 NO.sub.2                                                                             H      H    H   H                                    (CH.sub.2).sub.19 NO.sub.2                                                                             H      H    H   H                                    (CH.sub.2).sub.29 NO.sub.2                                                                             H      H    H   H                                    CH.sub.2 Cl              H      H    H   H                                    (CH.sub.2).sub.2 Cl      H      H    H   H                                    (CH.sub.2).sub.3 Cl      H      H    H   H                                    (CH.sub.2).sub.4 Cl      H      H    H   H                                    (CH.sub.2).sub.5 Cl      H      H    H   H                                    (CH.sub.2).sub.6 Cl      H      H    H   H                                    (CH.sub.2).sub.7 Cl      H      H    H   H                                    (CH.sub.2).sub.8 Cl      H      H    H   H                                    (CH.sub.2).sub.9 Cl      H      H    H   H                                    (CH.sub.2).sub.10 Cl     H      H    H   H                                    (CH.sub.2).sub.11 Cl     H      H    H   H                                    (CH.sub.2).sub.17 Cl     H      H    H   H                                    (CH.sub.2).sub.19 Cl     H      H    H   H                                    (CH.sub.2).sub.29 Cl     H      H    H   H                                    CH.sub.2 Br              H      H    H   H                                    (CH.sub.2).sub.2 Br      H      H    H   H                                    (CH.sub.2).sub.3 Br      H      H    H   H                                    (CH.sub.2).sub.4 Br      H      H    H   H                                    (CH.sub.2).sub.5 Br      H      H    H   H                                    (CH.sub.2).sub.6 Br      H      H    H   H                                    (CH.sub.2).sub.7 Br      H      H    H   H                                    (CH.sub.2).sub.8 Br      H      H    H   H                                    (CH.sub.2).sub.2 CHBrC.sub.6 H.sub.13                                                                  H      H    H   H                                    (CH.sub.2).sub.10 Br     H      H    H   H                                    (CH.sub.2).sub.11 Br     H      H    H   H                                    (CH.sub.2).sub.17 Br     H      H    H   H                                    (CH.sub.2).sub.19 Br     H      H    H   H                                    (CH.sub.2).sub.29 Br     H      H    H   H                                    CH.sub.2 F               H      H    H   H                                    (CH.sub.2).sub.2 F       H      H    H   H                                    (CH.sub.2).sub.3 F       H      H    H   H                                    (CH.sub.2).sub.4 F       H      H    H   H                                    (CH.sub.2).sub.5 F       H      H    H   H                                    (CH.sub.2).sub.6 F       H      H    H   H                                    (CH.sub.2).sub.7 F       H      H    H   H                                    (CH.sub.2).sub.8 F       H      H    H   H                                    (CH.sub.2).sub.9 F       H      H    H   H                                    (CH.sub.2).sub.10 F      H      H    H   H                                    (CH.sub.2).sub.11 F      H      H    H   H                                    (CH.sub.2).sub.11 F      COCH.sub.3                                                                           H    COCH                                                                              COCH.sub.3                           (CH.sub.2).sub.12 F      H      H    H   H                                    (CH.sub.2).sub.12 F      COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 CHFC.sub.7 H.sub.15                                                                   H      H    H   H                                    (CH.sub.2).sub.13 F      H      H    H   H                                    (CH.sub.2).sub.13 F      COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.12 CHF.sub.2                                                                            H      H    H   H                                    (CH.sub.2).sub.12 CHF.sub.2                                                                            COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.12 CF.sub.3                                                                             H      H    H   H                                    (CH.sub.2).sub.12 CF.sub.3                                                                             COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.14 F      H      H    H   H                                    (CH.sub.2).sub.14 F      COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.17 F      H      H    H   H                                    (CH.sub.2).sub.19 F      H      H    H   H                                    (CH.sub.2).sub.29 F      H      H    H   H                                    CH.sub.2 OCH.sub.3       H      H    H   H                                    CH.sub.2 OC.sub.2 H.sub.5                                                                              H      H    H   H                                    CH.sub.2 OC.sub.15 H.sub.31                                                                            H      H    H   H                                    (CH.sub.2).sub.2 OCH.sub.3                                                                             H      H    H   H                                    (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.2 OC.sub.15 H.sub.31                                                                    H      H    H   H                                    (CH.sub.2).sub.3 OCH.sub.3                                                                             H      H    H   H                                    (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.3 OC.sub.13 H.sub.27                                                                    H      H    H   H                                    (CH.sub.2).sub.4 OCH.sub.3                                                                             H      H    H   H                                    (CH.sub.2).sub.4 OC.sub.2 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.4 OC.sub.12 H.sub.25                                                                    H      H    H   H                                    (CH.sub.2).sub.5 OC.sub.8 H.sub.17                                                                     H      H    H   H                                    (CH.sub.2).sub.5 OC.sub.8 H.sub.17                                                                     COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.5 OC.sub.11 H.sub.23                                                                    H      H    H   H                                    (CH.sub.2).sub.6 OC.sub.7 H.sub.15                                                                     H      H    H   H                                    (CH.sub.2).sub.6 OC.sub.7 H.sub.15                                                                     COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.6 OC.sub.10 H.sub.21                                                                    H      H    H   H                                    (CH.sub.2).sub.7 OC.sub.6 H.sub.13                                                                     H      H    H   H                                    (CH.sub.2).sub.7 OC.sub.6 H.sub.13                                                                     COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.7 OC.sub.9 H.sub.19                                                                     H      H    H   H                                    (CH.sub.2).sub.8 OC.sub.5 H.sub.11                                                                     H      H    H   H                                    (CH.sub.2).sub.8 OC.sub.5 H.sub.11                                                                     COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.8 OC.sub.8 H.sub.17                                                                     H      H    H   H                                    (CH.sub.2).sub.9 OC.sub.7 H.sub.15                                                                     H      H    H   H                                    (CH.sub.2).sub.10 OC.sub.6 H.sub.13                                                                    H      H    H   H                                    (CH.sub.2).sub.11 OC.sub.5 H.sub.11                                                                    H      H    H   H                                    (CH.sub.2).sub.12 OC.sub.4 H.sub.9                                                                     H      H    H   H                                    (CH.sub.2).sub.13 OC.sub.3 H.sub.7                                                                     H      H    H   H                                    (CH.sub.2).sub.14 OC.sub.2 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.15 OCH.sub.3                                                                            H      H    H   H                                    CH.sub.2 OCH.sub.2 CHCH.sub.2                                                                          H      H    H   H                                    (CH.sub.2).sub.2 OCH.sub.2 CHCH.sub.2                                                                  H      H    H   H                                    (CH.sub.2).sub.3 OCH.sub.2 CHCH.sub.2                                                                  H      H    H   H                                    (CH.sub.2).sub.9 OCH.sub.2 CHCH.sub.2                                                                  H      H    H   H                                    (CH.sub.2).sub.13 OCH.sub.2 CHCH.sub.2                                                                 H      H    H   H                                    CH.sub.2 OCH.sub.2 CHCHCH.sub.3                                                                        H      H    H   H                                    (CH.sub.2).sub.2 OCH.sub.2 CHCHCH.sub.3                                                                H      H    H   H                                    (CH.sub.2).sub.3 OCH.sub.2 CHCHCH.sub.3                                                                H      H    H   H                                    (CH.sub.2).sub.9 OCH.sub.2 CHCHCH.sub.3                                                                H      H    H   H                                    (CH.sub.2).sub.12 OCH.sub.2 CHCHCH.sub.3                                                               H      H    H   H                                    CH.sub.2 OCH.sub.2 CHCHC.sub.7 H.sub.15                                                                H      H    H   H                                    (CH.sub.2).sub.2 OCH.sub.2 CHCHC.sub.7 H.sub.15                                                        H      H    H   H                                    (CH.sub.2).sub.3 OCH.sub.2 CHCHC.sub.7 H.sub.15                                                        H      H    H   H                                    (CH.sub.2).sub.6 OCH.sub.2 CHCHC.sub.7 H.sub.15                                                        H      H    H   H                                    (CH.sub.2).sub.9 OCH.sub.2 CHCHC.sub.7 H.sub.15                                                        H      H    H   H                                    CH.sub.2 OCH.sub.2 C CH  H      H    H   H                                    (CH.sub.2).sub.2 OCH.sub.2 C CH                                                                        H      H    H   H                                    (CH.sub.2).sub.3 OCH.sub.2 C CH                                                                        H      H    H   H                                    (CH.sub.2).sub.9 OCH.sub.2 C CH                                                                        H      H    H   H                                    (CH.sub.2).sub.11 CH(CH.sub.3)OCH.sub.2 C CH                                                           H      H    H   H                                    CH.sub.2 OCH.sub.2 C CCH.sub.3                                                                         H      H    H   H                                    (CH.sub.2).sub.2 OCH.sub.2 C CCH.sub.3                                                                 H      H    H   H                                    (CH.sub.2).sub.3 OCH.sub.2 C CCH.sub.3                                                                 H      H    H   H                                    (CH.sub.2).sub.9 OCH.sub.2 C CCH.sub.3                                                                 H      H    H   H                                    (CH.sub.2).sub.12 OCH.sub.2 C CCH.sub.3                                                                H      H    H   H                                    CH.sub.2 OCH.sub.2 C CC.sub.7 H.sub.15                                                                 H      H    H   H                                    (CH.sub.2).sub.2 OCH.sub.2 C CC.sub.7 H.sub.15                                                         H      H    H   H                                    (CH.sub.2).sub.3 OCH.sub.2 C CC.sub.7 H.sub.5                                                          H      H    H   H                                    (CH.sub.2).sub.6 OCH.sub.2 C CC.sub.7 H.sub.15                                                         H      H    H   H                                    (CH.sub.2).sub.9 OCH.sub.2 C CC.sub.7 H.sub.15                                                         H      H    H   H                                    CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                                     H      H    H   H                                    CH.sub.2 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                             H      H    H   H                                    CH.sub.2 O(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             H      H    H   H                                    (CH.sub.2).sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                             H      H    H   H                                    (CH.sub.2).sub.2 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.2 O(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                             H      H    H   H                                    (CH.sub.2).sub.3 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.3 O(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.4 OCH.sub.2 C.sub.6 H.sub.5                                                             H      H    H   H                                    (CH.sub.2).sub.4 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.4 O(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.5 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.5 O(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.5 O(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                     COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.6 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.7 OCH.sub.2 C.sub.6 H.sub.5                                                             H      H    H   H                                    (CH.sub.2).sub.7 OCH.sub.2 C.sub.6 H.sub.5                                                             COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.7 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.8 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.9 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    (CH.sub.2).sub.10 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.11 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.12 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.8 CH(C.sub.4 H.sub.9)O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                  H      H    H   H                                    (CH.sub.2).sub.14 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.15 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                    H      H    H   H                                    C.sub.17 H.sub.35        CH.sub.3                                                                             H    H   H                                    C.sub.17 H.sub.35        CH.sub.3                                                                             CH.sub.3                                                                           H   H                                    C.sub.17 H.sub.35        C.sub.18 H.sub.37                                                                    H    H                                        C.sub.17 H.sub.35        C.sub.18 H.sub.37                                                                    C.sub.18 H.sub.37                                                                  H   H                                    C.sub.17 H.sub.35        COCH.sub.3                                                                           H    H   H                                    C.sub.17 H.sub.35        COC.sub.17 H.sub.35                                                                  H    H   H                                    CH.sub.2 C.sub.6 H.sub.5 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.5 COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH(CH.sub.3)C.sub.6 H.sub.5                                                                            H      H    H   H                                    CHCHC.sub.6 H.sub.5      H      H    H   H                                    CHCHC.sub.6 H.sub.5      COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C CC.sub.6 H.sub.5       H      H    H   H                                    C CC.sub.6 H.sub.5       COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.5                                                                       H      H    H   H                                    CH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.5                                                                   H      H    H   H                                    CH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.5                                                                   COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.4 C.sub.6 H.sub.5                                                                       H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.5                                                                       H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.5                                                                       COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.6 C.sub.6 H.sub.5                                                                       H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.5                                                                       H      H    H   H                                    (CH.sub.2).sub.8 C.sub.6 H.sub.5                                                                       H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.5                                                                       H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.5                                                                       COCH.sub.3                                                                           H    GOCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.9 C.sub.6 H.sub.11                                                                      H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.12 C.sub.6 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.12 C.sub.6 H.sub.5                                                                      COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.13 C.sub.6 H.sub.5                                                                      H      H    W   H                                    (CH.sub.2).sub.15 C.sub.6 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.19 C.sub.6 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.29 C.sub.6 H.sub.5                                                                      H      H    H   H                                    C.sub.6 H.sub.4 -3-CH.sub.3                                                                            H      H    H   H                                    C.sub.6 H.sub.4 -4-CH.sub.3                                                                            H      H    H   H                                    C.sub.6 H.sub.4 -3-C.sub.2 H.sub.5                                                                     H      H    H   H                                    C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                                     H      H    H   H                                    C.sub.6 H.sub.4 -3-C.sub.3 H.sub.7                                                                     H      H    H   H                                    C.sub.6 H.sub.4 -2-C.sub.3 H.sub.7                                                                     H      H    H   H                                    C.sub.6 H.sub.4 -4-C.sub.3 H.sub.7                                                                     H      H    H   H                                    C.sub.6 H.sub.4 -3-C.sub.4 H.sub.9                                                                     H      H    H                                        C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                                     H      H    H   H                                    C.sub.6 H.sub.4 -3-C.sub.6 H.sub.13                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -4-C.sub.9 H.sub.19                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -4-C.sub.9 H.sub.19                                                                    COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.6 H.sub.10 -3-C.sub.6 H.sub.13                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -3-C.sub.10 H.sub.21                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-C.sub.10 H.sub.21                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -3-C.sub.12 H.sub.25                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-C.sub.12 H.sub.25                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -3-C.sub.20 H.sub.41                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-C.sub.20 H.sub.41                                                                   H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-CH.sub.3                                                                   H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CH.sub.3                                                                   H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.2 H.sub.5                                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.3 H.sub.7                                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.3 H.sub.7                                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.4 H.sub.9                                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.6 H.sub.13                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-C.sub.4 H.sub.9                                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-C.sub.6 H.sub.13                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2 ).sub.3 CH(CH.sub.3).sub.2                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2 ).sub.3 CH(CH.sub.3).sub.2                                       COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.7 H.sub.15                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.7 H.sub.15                                                           COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                           COCH.sub.3                                                                           H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                           COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                           CH.sub.3                                                                             CH.sub.3                                                                           H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-C.sub.8 H.sub.17                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-C.sub.8 H.sub.17                                                           COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.8 H.sub.17                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.8 H.sub.17                                                           COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.10 H.sub.21                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.10 H.sub.21                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.12 H.sub.25                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.12 H.sub.25                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.12 H.sub.25                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -3-C.sub.20 H.sub.41                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C.sub.20 H.sub.41                                                          H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-CH.sub.3                                                           H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.3                                                           H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.7 H.sub.12 -3-C.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.3 H.sub.7                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.3 H.sub.7                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-C.sub.7 H.sub.15                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-C.sub.7 H.sub.15                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.7 H.sub.15                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.7 H.sub.15                                                   COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.11 H.sub.23                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.11 H.sub.23                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.20 H.sub.41                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.20 H.sub.41                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-CH.sub.3                                                           H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.3                                                           H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C.sub.3 H.sub.7                                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C.sub.3 H.sub.7                                                    H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-C.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-C.sub.4 H.sub.9                                                   COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                    COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                   COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                   COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -2-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-C.sub.20 H.sub.41                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.20 H.sub.41                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-CH.sub.3                                                           H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-CH.sub.3                                                           H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C.sub.3 H.sub.7                                                    H      H    H   H                                    CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -3-C.sub.3 H.sub.7                                               H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-C.sub.3 H.sub.7                                                    H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -2-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-C.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C.sub.20 H.sub.41                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-C.sub.20 H.sub.41                                                  H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-CH.sub.3                                                           H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-CH.sub.3                                                           H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-C.sub.3 H.sub.7                                                    H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C.sub.3 H.sub.7                                                    H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                    COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.5 C.sub.6 H.sub.4 -2-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C.sub.10 H.sub.21                                                  H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.10 -4-C.sub.10 H.sub.21                                                 H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C.sub.12 H.sub.25                                                  H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-C.sub.20 H.sub.41                                                  H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C.sub.20 H.sub.41                                                  H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-C.sub.7 H.sub.15                                                   H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                    COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                   H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                   COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 CHC(C.sub.3 H.sub.7)C.sub.6 H.sub.10 -4-C.sub.6 H.sub.13                              H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -3-C.sub.5 H.sub.11                                                   H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-C.sub.4 H.sub.9                                                    H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -3-C.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-C.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -3-CH.sub.3                                                          H      H    H   H                                    C.sub.6 H.sub.4 -3-CHCH.sub.2                                                                          H      H    H   H                                    C.sub.6 H.sub.4 -4-CHCH.sub.2                                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-CHCH.sub.2                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CHCH.sub.2                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-CHCHCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CHCHCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-CHCHCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-CHCHC.sub.8 H.sub.17                                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CHCHC.sub.8 H.sub.17                                                       H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-CHCHCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-CHCHC.sub.8 H.sub.17                                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CHCHC.sub.8 H.sub.17                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-CHCHC.sub.8 H.sub.17                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-CHCHC.sub.8 H.sub.17                                               H      H    H   H                                    CH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -4-CHCHC.sub.8 H.sub.17                                           H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -2-CHCHC.sub.8 H.sub.17                                               H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-CHCHC.sub.8 H.sub.17                                               H      H    H   H                                    CH.sub.2 CH(C.sub.2 H.sub.5)-C.sub.5 H.sub.8 -3-CHCHC.sub.8 H.sub.17                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-CHCHC.sub.8 H.sub.17                                               H      H    H   H                                    CHCH(CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CHCHC.sub.8 H.sub.17                                           H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-CHCHC.sub.8 H.sub.17                                               H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 CHCHC.sub.4 H.sub.9                               H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-CHCH.sub.2                                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -3-CHCHCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-CH.sub.2 CHCH.sub.2                                                H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-CHCHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-(CH.sub.2).sub.4 CHCHC.sub.4 H.sub.9                               H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CHCHC.sub.2 H.sub.5                               H      H    H   H                                    C.sub.6 H.sub.4 -3-C CH  H      H    H   H                                    C.sub.6 H.sub.4 -4-C CH  H      H    H   H                                    C.sub.6 H.sub.10 -4-C CH H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-C CH                                                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C CH                                                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-C CCH.sub.3                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-C CCH.sub.3                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-(CH.sub.2).sub.6 C CC.sub.2 H.sub.5                                        H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 C CC.sub.5 H.sub.11                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-(CH.sub.2).sub.3 C CC.sub.5 H.sub.11                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.3 C CC.sub.5 H.sub.11                                      H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C CCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-C CCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 C CCH.sub.3                                       H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-(CH.sub.2).sub.3 C CC.sub.5 H.sub.11                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-C CC.sub.8 H.sub.17                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-C CCH.sub.3                                                        H      H    H   H                                    CH(C.sub.2 H.sub.5)C.sub.6 H.sub.4 -4-C CCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-(CH.sub.2).sub.4 C CC.sub.4 H.sub.9                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -2-C CC.sub.8 H.sub.17                                                H      H    H   H                                    CH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.10 -2-(CH.sub.2).sub.3 C CC.sub.5          H.sub.11                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-C CC.sub.8 H.sub.17                                                H      H    H   H                                    CH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.10 -4-(CH.sub.2).sub.3 C CC.sub.5          H.sub.11                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C CCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-CH.sub.2 C CH                                                      H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-C CC.sub.8 H.sub.17                                                H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 C CH                                              H      H    H   H                                    (CH.sub.2).sub.4 C.sub.5 H.sub.8 -4-(CH.sub.2).sub.8 C CH                                              H      H    H   H                                    CH.sub.2 CHCHCH.sub.2 C.sub.5 H.sub.8 -4-(CH.sub.2).sub.8 C                                            HH     H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -2-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -2-C CH                                                               COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-CH.sub.2 C CH                                                      H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C CCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)C.sub.6 H.sub.4 -3-(CH.sub.2).sub.2 C     C.sub.6 H.sub.13         H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-C CC.sub.8 H.sub.17                                                H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-C CH                                                               H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-CH.sub.2 C CH                                                      H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-C CCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.3 CH(C.sub.3 H.sub.7)C.sub.6 H.sub.4 -3-(CH.sub.2).sub.5 C     C.sub.3 H.sub.7          H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-C CC.sub.8 H.sub.17                                                H      H    H   H                                    (CH.sub.2).sub.7 C.sub.8 H.sub.12 -4-(CH.sub.2).sub.4 C                                                HC.sub.4 H.sub.9                                                                     H    H   H                                    C C(CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -4-C CC.sub.8 H.sub.17                                 H      H    H   H                                    C.sub.6 H.sub.4 -3-OCH.sub.3                                                                           H      H    H   H                                    C.sub.6 H.sub.4 -4-OCH.sub.3                                                                           H      H    H   H                                    C.sub.6 H.sub.4 -3-OC.sub.2 H.sub.5                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.2 H.sub.5                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -3-OC.sub.3 H.sub.7                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.3 H.sub.7                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -3-OC.sub.4 H.sub.9                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -2-OC.sub.4 H.sub.9                                                                    H      H    H   H                                    C.sub.6 H.sub.10 -3-OC.sub.4 H.sub.9                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -3-OC.sub.6 H.sub.13                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.8 H.sub.17                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.8 H.sub.17                                                                   COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.6 H.sub.4 -3-OC.sub.10 H.sub.21                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.10 H.sub.21                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -3-OC.sub.10 H.sub.21                                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           C.sub.6 H.sub.4 -3-OC.sub.12 H.sub.25                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.12 H.sub.25                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -3-OC.sub.20 H.sub.41                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -4-OC.sub.20 H.sub.41                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OCH.sub.3                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OCH.sub.3                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OC.sub.2 H.sub.5                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.2 H.sub.5                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OC.sub.3 H.sub.7                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.3 H.sub.7                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-OC.sub.4 H.sub.9                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OC.sub.4 H.sub.9                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.5 H.sub.11                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.5 H.sub.11                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.7 H.sub.15                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.7 H.sub.15                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 CHCH.sub.2                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 CHCH.sub.2                                               COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.8 H.sub.17                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.8 H.sub.17                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.9 H.sub.19                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.9 H.sub.19                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -3-OC.sub.6 H.sub.13                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OC.sub.10 H.sub.21                                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.10 H.sub.21                                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.11 H.sub.23                                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.11 H.sub.23                                                         COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.8 -3-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.6 H.sub.13                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.7 H.sub.15                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.7 H.sub.15                                                  COCH.sub.3                                                                           H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.7 H.sub.15                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.7 H.sub.15                                                  COCH.sub.3                                                                           H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.8 H.sub.17                                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.8 H.sub.17                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.10 H.sub.21                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.10 H.sub.21                                                 H      H    H   H                                    CHCHC.sub.6 H.sub.4 -4-OC.sub.10 H.sub.21                                                              COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.11 H.sub.23                                                 COCH.sub.3                                                                           H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.11 H.sub.23                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.11 H.sub.23                                                 COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -2-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OC.sub.20 H.sub.41                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OC.sub.20 H.sub.41                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.5 H.sub.11                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.5 H.sub.11                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.6 H.sub.13                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.10 H.sub.21                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -2-OC.sub.10 H.sub.21                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.10 H.sub.21                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.11 H.sub.23                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.11 H.sub.23                                                 COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.20 H.sub.41                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OC.sub.20 H.sub.41                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.8 H.sub.14 -5-OC.sub.20 H.sub.41                                                H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OC.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OC.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OC.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OC.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                   COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OC.sub.6 H.sub.13                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.10 -3-OC.sub.6 H.sub.13                                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OC.sub.10 H.sub.21                                                 H      H    H   H                                    CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-OC.sub.10 H.sub.21                                            H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OC.sub.20 H.sub.41                                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OC.sub.20 H.sub.41                                                 H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -2-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-OC.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-OC.sub.2 H.sub.5                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-OC.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-OC.sub.3 H.sub.7                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-OC.sub.6 H.sub.13                                                  H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                  H      H    H   H                                    C C(CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OC.sub.10 H.sub.21                                              H      H    H   H                                    C C(CH.sub.2).sub.3 C.sub.6 H.sub.10 -3-OC.sub.10 H.sub.21                                             H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-OC.sub.10 H.sub.21                                                 H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-OC.sub.12 H.sub.25                                                 H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-OC.sub.20 H.sub.41                                                 H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-OC.sub.20 H.sub.41                                                 H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-OCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-OCH.sub.3                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-OC.sub.7 H.sub.15                                                  H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                  H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -2-OC.sub.5 H.sub.11                                                  H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -3-OC.sub.5 H.sub.11                                                  H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-OC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -3-OC.sub.3 H.sub.7                                                  H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-OC.sub.2 H.sub.5                                                  H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -3-OCH.sub.3                                                         H      H    H   H                                    C.sub.6 H.sub.4 -3-OCHCH.sub.2                                                                         H      H    H   H                                    C.sub.6 H.sub.4 -4-OCHCH.sub.2                                                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OCHCH.sub.2                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OCHCH.sub.2                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OCH.sub.2 CHCH.sub.2                                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OCH.sub.2 CHCH.sub.2                                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.4 CHCHC.sub.4 H.sub.9                                      H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 CHCHCH.sub.3                                             H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OCH.sub.2 CHCH.sub.2                                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OCH.sub.2 CHCH.sub.2                                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-OCH.sub.2 CHCH.sub.2                                              H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.4 CHCHC.sub.4                                      H.sub.9                                                                              H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 CHCHC.sub.4                                      H.sub.9                                                                              H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OCH.sub.2 CHCH.sub.2                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OCH.sub.2 CHCH.sub.2                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.4 CHCHC.sub.4                                      H.sub.9                                                                              H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 CHCHC.sub.2                                      H.sub.5                                                                              H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -3-OCH.sub.2 CHCH.sub.2                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-OCH.sub.2 CHCH.sub.2                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.4 CHCHC.sub.4                                      H.sub.9                                                                              H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 CHCHC.sub.4                                      H.sub.9                                                                              H    H   H                                    C.sub.6 H.sub.4 -3-OC CH H      H    H   H                                    C.sub.6 H.sub.4 -4-OC CH H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OC CH                                                                      H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OC CH                                                                      H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OCH.sub.2 C CH                                                             H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OCH.sub.2 C CH                                                             H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.4 C CC.sub.4 H.sub.9                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C CC.sub.4 H.sub.9                                       H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.2 C.sub.5 H.sub.8 -2-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.6 C                                                HC.sub.2 H.sub.5                                                                     H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C                                                HC.sub.4 H.sub.9                                                                     H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.2 C                                                HC.sub.6 H.sub.13                                                                    H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 C                                                HCH.sub.3                                                                            H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -2-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.2 C                                                HC.sub.6 H.sub.13                                                                    H    H   H                                    CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C CC.sub.4         H.sub.9                  H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)C.sub.6 H.sub.4 -4-OCH.sub.2 C                                     HH     H    H   H                                    (CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)C.sub.6 H.sub.10 -4-OCH.sub.2 C                                    HH     H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.5 C                                                HC.sub.3 H.sub.7                                                                     H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C                                                HC.sub.4 H.sub.9                                                                     H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.5 C                                                HC.sub.3 H.sub.7                                                                     H    H   H                                    (CH.sub.2).sub.2 C C(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7     C CCH.sub.3              H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -3-OCH.sub.2 C CH                                                     H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.2 C                                                HCH.sub.3                                                                            H    H   H                                    (CH.sub.2).sub.5 CH(C.sub.3 H.sub.7)C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.3      C CC.sub.5 H.sub.11      H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C                                                HC.sub.2 H.sub.5                                                                     H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -3-OCH.sub.2 C CH                                                    H      H    H   H                                    (CH.sub.2).sub.3 C C(CH.sub.2).sub.6 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.2     C CCH.sub.3              H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -2-O(CH.sub.2).sub.2 C CC.sub.6             H.sub.13                 H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.2 C CC.sub.6             H.sub.13                 H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 C                                               HH     H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.2 C CC.sub.2                                      H.sub.5                                                                              H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.2 C                                               HCH.sub.3                                                                            H    H   H                                    (CH.sub.2).sub.4 CHCH(CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.2     C CC.sub.6 H.sub.13     H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 C                                               HH     H    H   H                                    C.sub.6 H.sub.4 -4-OCH.sub.2 C.sub.6 H.sub.5                                                           H      H    H   H                                    C.sub.6 H.sub.10 -4-OCH.sub.2 C.sub.6 H.sub.5                                                          H      H    H   H                                    C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                   H      H    H   H                                    C.sub.6 H.sub.10 -4-O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                                  H      H    H   H                                    C.sub.6 H.sub.4 -2-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                                   H      H    H   H                                    C.sub.6 H.sub.10 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                                  H      H    H   H                                    C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 C.sub.6 H.sub.5                                                   H      H    H   H                                    C.sub.6 H.sub.10 -4-O(CH.sub.2).sub.10 C.sub.6 H.sub.5                                                 H      H    H   H                                    C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.12 C.sub.6 H.sub.5                                                  H      H    H   H                                    C.sub.6 H.sub.10 -4-O(CH.sub.2).sub.14 C.sub.6 H.sub.5                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -2-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                  H      H    H   H                                    (CH.sub.2).sub.5 CH(CH.sub.3)C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C.sub.6     H.sub.5                  H      H    H   H                                    CH.sub.2 CHCHCH.sub.2 CH(C.sub.2 H.sub.5)C.sub.6 H.sub.4 -4-O(CH.sub.2).su    b.4 C.sub.6 H.sub.5      H      H    H   H                                    CH.sub.2 CHCHCH.sub.2 CH(C.sub.2 H.sub.5)C.sub.6 H.sub.10 -4-O(CH.sub.2).s    ub.4 C.sub.6 H.sub.5     H      H    H   H                                    (CH.sub.2).sub.3 C C(CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-O(CH.sub.2).sub.4     C.sub.6 H.sub.5         H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.5 C.sub.5 H.sub.5                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.5                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 C.sub.6 H.sub.5                                  H      H    H   H                                    (CH.sub.2).sub.5 CH(CH.sub.3)C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.10            C.sub.6 H.sub.5          H      H    H   H                                    CH.sub.2 CHCHCH.sub.2 CH(C.sub.2 H.sub.5)C.sub.6 H.sub.4 -4-O(CH.sub.2).su    b.12 C.sub.6 H.sub.5     H      H    H   H                                    CH.sub.2 CHCHCH.sub.2 CH(C.sub.2 H.sub.5)C.sub.6 H.sub.10 -4-O(CH.sub.2).s    ub.13 C.sub.6 H.sub.5    H      H    H   H                                    (CH.sub.2).sub.3 C C(CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.3     C.sub.6 H.sub.5          H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 C.sub.6 H.sub.5                                  H      H    H   H                                    C.sub.6 H.sub.4 -4-COCH.sub.3                                                                          H      H    H   H                                    C.sub.6 H.sub.10 -4-COCH.sub.3                                                                         H      H    H   H                                    C.sub.6 H.sub.4 -4-COC.sub.2 H.sub.5                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-COC.sub.5 H.sub.11                                                                  H      H    H   H                                    C.sub.6 H.sub.10 -4-COC.sub.7 H.sub.15                                                                 H      H    H   H                                    C.sub.6 H.sub.4 -4-COC.sub.13 H.sub.27                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-COCH.sub.3                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -2-COCH.sub.3                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-COCH.sub.3                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -3-COCH.sub.3                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-COCH.sub.3                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-COCH.sub.3                                                                H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-COCH.sub.3                                                         H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-COC.sub.6 H.sub.13                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-COC.sub.9 H.sub.19                                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-COC.sub.10 H.sub.21                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-COC.sub.3 H.sub.7                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-COC.sub.9 H.sub.19                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-COC.sub.3 H.sub.7                                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-COCH.sub.3                                                         H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-COC.sub.5 H.sub.11                                     H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-COC.sub.5 H.sub.11                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-COCH.sub.3                                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-COCH.sub.3                                                        H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-COCH.sub.3                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-COC.sub.7 H.sub.15                                                         H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -2-COC.sub.7 H.sub.15                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -3-COC.sub.7 H.sub.15                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-COC.sub.7 H.sub.15                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-COC.sub.7 H.sub.15                                                H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-COC.sub.3 H.sub.7                                                 H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-COC.sub.2 H.sub.5                               H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-COCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-COCH.sub.3                                         H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-COC.sub.7 H.sub.15                                 H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-COCH.sub.3                                            H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-COC.sub.4 H.sub.9                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-COC.sub.9 H.sub.19                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-COC.sub.9 H.sub.19                                                H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-COC.sub.13 H.sub.27                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-COC.sub.17 H.sub.35                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-COC.sub.18 H.sub.37                                                H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCOCH.sub.3                                                                        H      H    H   H                                    C.sub.6 H.sub.10 -4-NHCOCH.sub.3                                                                       H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCOC.sub.2 H.sub.5                                                                 H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCOC.sub.5 H.sub.11                                                                H      H    H   H                                    C.sub.6 H.sub.10 -4-NHCOC.sub.7 H.sub.15                                                               H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCOC.sub.13 H.sub.27                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-NHCOCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-NHCOCH.sub.3                                                              H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-NHCOCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-NHCOCH.sub.3                                                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOC.sub.9 H.sub.19                                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOC.sub.9 H.sub.19                                               COOC(CH.sub.3).sub.3                                                                 H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-NHCOC.sub.3 H.sub.7                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-NHCOC.sub.3 H.sub.7                                               H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-NHCOCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NHCOC.sub.5 H.sub.11                                   H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NHCOC.sub.5 H.sub.11                                       H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-NHCOCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-NHCOCH.sub.3                                                      H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-NHCOCH.sub.3                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-NHCOC.sub.7 H.sub.15                                                       H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-NHCOC.sub.7 H.sub.15                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-NHCOC.sub.7 H.sub.15                                              H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-NHCOC.sub.3 H.sub.7                                               H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-NHCOC.sub.2            H.sub.5                  H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-NHCOCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-NHCOCH.sub.3                                       H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-NHCOC.sub.7 H.sub.15                               H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-NHCOCH.sub.3                                          H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-NHCOC.sub.4 H.sub.9                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-NHCOC.sub.9 H.sub.19                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-NHCOC.sub.9 H.sub.19                                              H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-NHCOC.sub.13 H.sub.27                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOC.sub.17 H.sub.25                                              H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-NHCOC.sub.18 H.sub.37                                              H      H    H   H                                    C.sub.6 H.sub.4 -4-OCOCH.sub.3                                                                         H      H    H   H                                    C.sub.6 H.sub.10 -4-OCOCH.sub.3                                                                        H      H    H   H                                    C.sub.6 H.sub.4 -4-OCOC.sub.2 H.sub.5                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -2-OCOC.sub.5 H.sub.11                                                                 H      H    H   H                                    C.sub.6 H.sub.4 -4-OCOC.sub.5 H.sub.11                                                                 H      H    H   H                                    C.sub.6 H.sub.10 -4-OCOC.sub.7 H.sub.15                                                                H      H    H   H                                    C.sub.6 H.sub.4 -4-OCOC.sub.13 H.sub.27                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OCOCH.sub.3                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-OCOCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OCOCH.sub.3                                                                H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OCOCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OCOC.sub.3 H.sub.7                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-OCOC.sub.3 H.sub.7                                                H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OCOCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-OCOC.sub.5 H.sub.11                                    H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-OCOC.sub.5 H.sub.11                                        H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-OCOCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-OCOCH.sub.3                                                       H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-OCOCH.sub.3                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-OCOC.sub.7 H.sub.15                                                        H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OCOC.sub.7 H.sub.15                                                        H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OCOC.sub.7 H.sub.15                                                        H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.4 -4-OCOC.sub.7 H.sub.15                                                H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-OCOC.sub.7 H.sub.15                                               H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-OCOC.sub.3 H.sub.7                                                H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9 C.sub.6 H.sub.4 -4-OCOC.sub.2                                      H.sub.5                                                                              H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -2-OCOCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -3-OCOCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-OCOCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-OCOCH.sub.3                                        H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-OCOC.sub.7 H.sub.15                                H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-OCOCH.sub.3                                           H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-OCOC.sub.4 H.sub.9                                                H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-OCOC.sub.9 H.sub.19                                                H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-OCOC.sub.9 H.sub.19                                               H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-OCOC.sub.13 H.sub.27                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OCOC.sub.17 H.sub.35                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OCOC.sub.18 H.sub.37                                               H      H    H   H                                    C.sub.6 H.sub.4 -4-COOCH.sub.3                                                                         H      H    H   H                                    C.sub.6 H.sub.10 -4-COOCH.sub.3                                                                        H      H    H   H                                    C.sub.6 H.sub.4 -4-COOC.sub.2 H.sub.5                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -4-COOC.sub.4 H.sub.9                                                                  H      H    H   H                                    C.sub.6 H.sub.10 -4-COOC.sub.8 H.sub.17                                                                H      H    H   H                                    C.sub.6 H.sub.10 -3-COOC.sub.8 H.sub.17                                                                H      H    H   H                                    C.sub.6 H.sub.10 -4-COOC.sub.8 H.sub.17                                                                H      H    H   H                                    C.sub.6 H.sub.4 -4-COOC.sub.14 H.sub.29                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-COOCH.sub.3                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-COOCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-COOCH.sub.3                                                                H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-COOCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-COOC.sub.4 H.sub.9                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-COOC.sub.4 H.sub.9                                                H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-COOCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-COOC.sub.6 H.sub.13                                    H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-COOC.sub.6 H.sub.13                                        H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -2-COOCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -3-COOCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-COOCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-COOCH.sub.3                                                       H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-COOCH.sub.3                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-COOC.sub.8 H.sub.17                                                        H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-COOC.sub.8 H.sub.17                                                H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-COOC.sub.8 H.sub.17                                               H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-COOC.sub.4 H.sub.9                                                H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-COOC.sub.3                                      H.sub.7                                                                              H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-COOCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-COOCH.sub.3                                        H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-COOC.sub.8 H.sub.17                                H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-COOCH.sub.3                                           H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-COOC.sub.5 H.sub.11                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-COOC.sub.10 H.sub.21                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-COOC.sub.10 H.sub.21                                              H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-COOC.sub.14 H.sub.29                                  H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-COOC.sub.18 H.sub.37                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -2-COOC.sub.19 H.sub.39                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-COOC.sub.19 H.sub.39                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-COOC.sub.19 H.sub.39                                               H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCOOCH.sub.3                                                                       H      H    H   H                                    C.sub.6 H.sub.10 -4-NHCOOCH.sub.3                                                                      H      H    H   H                                    C.sub.6 H.sub.4 -2-NHCOOC.sub.2 H.sub.5                                                                H      H    H   H                                    C.sub.6 H.sub.4 -3-NHCOOC.sub.2 H.sub.5                                                                H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCOOC.sub.2 H.sub.5                                                                H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCOOC.sub.4 H.sub.9                                                                H      H    H   H                                    C.sub.6 H.sub.10 -4-NHCOOC.sub.8 H.sub.17                                                              H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCOOC.sub.14 H.sub.29                                                              H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-NHCOOCH.sub.3                                                              H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-NHCOOCH.sub.3                                                             H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-NHCOOCH.sub.3                                                              H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -2-NHCOOCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOOCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-NHCOOC.sub.4 H.sub.9                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-NHCOOC.sub.4 H.sub.9                                              H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-NHCOOCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NHCOOC.sub.6 H.sub.13                                  H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NHCOOC.sub.6 H.sub.13                                      H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-NHCOOCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-NHCOOCH.sub.3                                                     H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-NHCOOCH.sub.3                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-NHCOOC.sub.8 H.sub.17                                                      H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-NHCOOC.sub.8 H.sub.17                                              H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.17 -4-NHCOOC.sub.8 H.sub.17                                             H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-NHCOOC.sub.4 H.sub.9                                              H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-NHCOOC.sub.3           H.sub.7                  H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-NHCOOCH.sub.3                                                     H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-NHCOOCH.sub.3                                      H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-NHCOOC.sub.8 H.sub.17                              H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-NHCOOCH.sub.3                                         H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-NHCOOC.sub.5 H.sub.11                                             H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-NHCOOC.sub.10 H.sub.21                                             H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-NHCOOC.sub.10 H.sub.21                                            H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-NHCOOC.sub.14 H.sub.29                                H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOOC.sub.18 H.sub.37                                             H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-NHCOOC.sub.19 H.sub.39                                             H      H    H   H                                    C.sub.6 H.sub.4 -4-NHCH.sub.3                                                                          H      H    H   H                                    C.sub.6 H.sub.10 -4-NHCH.sub.3                                                                         H      H    H   H                                    C.sub.6 H.sub.4 -4-NHC.sub.2 H.sub.5                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-NHC.sub.4 H.sub.9                                                                   H      H    H   H                                    C.sub.6 H.sub.10 -4-NHC.sub.8 H.sub.17                                                                 H      H    H   H                                    C.sub.6 H.sub.4 -4-NHC.sub.14 H.sub.29                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-NHCH.sub.3                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-NHCH.sub.3                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-NHCH.sub.3                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-N(CH.sub.3)C.sub.10 H.sub.21                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-N(CH.sub.3)C.sub.10 H.sub.21                                               COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCH.sub.3                                                         H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHC.sub.10 H.sub.21                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-NHC.sub.4 H.sub.9                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-NHC.sub.4 H.sub.9                                                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-NHCH.sub.3                                                         H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -2-NHC.sub.6 H.sub.13                                     H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NHC.sub.6 H.sub.13                                     H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NHC.sub.6 H.sub.13                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-NHCH.sub.3                                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-NHCH.sub.3                                                        H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-NHCH.sub.3                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-NHC.sub.8 H.sub.17                                                         H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-NHC.sub.8 H.sub.17                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-NHC.sub.8 H.sub.17                                                H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-NHC.sub.4 H.sub.9                                                 H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-NHC.sub.3 H.sub.7                               H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-NHCH.sub.3                                                        H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-NHCH.sub.3                                         H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-NHC.sub.8 H.sub.17                                 H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-NHCH.sub.3                                            H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-NHC.sub.5 H.sub.11                                                H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-NHC.sub.10 H.sub.21                                                H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-NHC.sub.10 H.sub.21                                               H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-NHC.sub.14 H.sub.29                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHC.sub.18 H.sub.37                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-NHC.sub.19 H.sub.39                                                H      H    H   H                                    C.sub.6 H.sub.4 -4-SCH.sub.3                                                                           H      H    H   H                                    C.sub.6 H.sub.10 -4-SCH.sub.3                                                                          H      H    H   H                                    C.sub.6 H.sub.4 -4-SC.sub.2 H.sub.5                                                                    H      H    H   H                                    C.sub.6 H.sub.4 -4-SC.sub.2 H.sub.5                                                                    H      H    H   H                                    C.sub.6 H.sub.10 -4-SC.sub.8 H.sub.17                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -4-SC.sub.8 H.sub.17                                                                   H      H    H   H                                    C.sub.6 H.sub.4 -4-SC.sub.8 H.sub.17                                                                   COCH.sub.3                                                                           H    H   H                                    C.sub.6 H.sub.4 -4-SC.sub.14 H.sub.29                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-SCH.sub.3                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-SCH.sub.3                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-SCH.sub.3                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-SCH.sub.3                                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-SC.sub.7 H.sub.15                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-SC.sub.7 H.sub.15                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-SCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-SC.sub.4 H.sub.9                                                   H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-SC.sub.4 H.sub.9                                                  H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-SCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.10 -3-SC.sub.6 H.sub.13                                     H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-SC.sub.6 H.sub.13                                          H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-SCH.sub.3                                                          H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-SCH.sub.3                                                         H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-SCH.sub.3                                             H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-SC.sub.8 H.sub.17                                                          H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-SC.sub.8 H.sub.17                                                  H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-SC.sub.8 H.sub.17                                                 H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-SC.sub.4 H.sub.9                                                  H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-SC.sub.3 H.sub.7                                H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-SCH.sub.3                                                         H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-SCH.sub.3                                          H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-SC.sub.8 H.sub.17                                  H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-SCH.sub.3                                             H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-SC.sub.5 H.sub.11                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-SC.sub.10 H.sub.21                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-SC.sub.10 H.sub.21                                                H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-SC.sub.14 H.sub.29                                    H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-SC.sub.18 H.sub.37                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-SC.sub.19 H.sub.39                                                 H      H    H   H                                    C.sub.6 H.sub.4 -4-CONHCH.sub.3                                                                        H      H    H   H                                    C.sub.6 H.sub.10 -4-CONHCH.sub.3                                                                       H      H    H   H                                    C.sub.6 H.sub.4 -4-CONHC.sub.2 H.sub.5                                                                 H      H    H   H                                    C.sub.6 H.sub.4 -4-CONHC.sub.4 H.sub.9                                                                 H      H    H   H                                    C.sub.6 H.sub.10 -4-CONHC.sub.8 H.sub.17                                                               H      H    H   H                                    C.sub.6 H.sub.4 -4-CONHC.sub.14 H.sub.29                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CONHCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-CONHCH.sub.3                                                              H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -2-CONHCH.sub.3                                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-CONHCH.sub.3                                                               H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CONHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-CONHC.sub.4 H.sub.9                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-CONHC.sub.4 H.sub.9                                               H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-CONHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-CONHC.sub.6 H.sub.13                                   H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-CONHC.sub.6 H.sub.13                                       H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-CONHCH.sub.3                                                       H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-CONHCH.sub.3                                                      H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-CONHCH.sub.3                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CONHC.sub.8 H.sub.17                                                       H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-CONHC.sub.8 H.sub.17                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-CONHC.sub.8 H.sub.17                                              H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-CONHC.sub.4 H.sub.9                                               H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-CONHC.sub.3            H.sub.7                  H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-CONHCH.sub.3                                                      H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-CONHCH.sub.3                                       H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-CONHC.sub.8 H.sub.17                               H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-CONHCH.sub.3                                          H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-CONHC.sub.5 H.sub.11                                              H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-CONHC.sub.10 H.sub.21                                              H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-CONHC.sub.10 H.sub.21                                             H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-CONHC.sub.14 H.sub.29                                 H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CONHC.sub.18 H.sub.37                                              H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-CONHC.sub.19 H.sub.39                                              H      H    H   H                                    C.sub.6 H.sub.4 -4-CH.sub.2 Br                                                                         H      H    H   H                                    C.sub.6 H.sub.10 -4-CH.sub.2 Br                                                                        H      H    H   H                                    C.sub.6 H.sub.4 -2-CH.sub.2 Br                                                                         H      H    H   H                                    C.sub.6 H.sub.10 -3-CH.sub.2 Br                                                                        H      H    H   H                                    C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 F                                                                  H      H    H   H                                    C.sub.6 H.sub.4 -3-(CH.sub.2).sub.4 Cl                                                                 H      H    H   H                                    C.sub.6 H.sub.10 -4-(CH.sub.2).sub.2 CHFC.sub.3 H.sub.7                                                H      H    H   H                                    C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CHBrC.sub.6 H.sub.13                                               H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 Br                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -2-CF.sub.3                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -3-CF.sub.3                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-CF.sub.3                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 Cl                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-CH.sub.2 Br                                                                H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 F                                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 F                                                         COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.2 C.sub.7 H.sub.15                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.2 C.sub.7 H.sub.15                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 Br                                                        H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 Br                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.4 Br                                               H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-CH.sub.2 Cl                                                        H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-CH.sub.2 Br                                                        H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-(CH.sub.2).sub.2 CHClC.sub.3      H.sub.7                  H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-CH.sub.2 F                                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-CH.sub.2 Br                                                       H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-CH.sub.2 Br                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 CHFC.sub.4 H.sub.9                                        H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CHClC.sub.2 H.sub.5                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-(CH.sub.2).sub.5 CHClC.sub.2                                      H.sub.5                                                                              H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -3-(CH.sub.2).sub.4 Cl                                               H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -2-CH.sub.2 CHBrCH.sub    .3                       H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-CH.sub.2 Br                                                       H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-CH.sub.2 Br                                        H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -3-(CH.sub.2).sub.3          CHFC.sub.4 H.sub.9       H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -4-CH.sub.2 Br                                           H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 CHClC.sub.2                                      H.sub.5                                                                              H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -3-(CH.sub.2).sub.10 Cl                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.7 CHClC.sub.2                                      H.sub.5                                                                              H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -3-(CH.sub.2).sub.3             CHFC.sub.10 H.sub.21     H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -3-(CH.sub.2).sub.9 CBr.sub.2 C.sub.8        H.sub.17                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.18 CF.sub.3                                         H      H    H   H                                    C.sub.6 H.sub.4 -4-NH.sub.2                                                                            H      H    H   H                                    C.sub.6 H.sub.10 -4-NH.sub.2                                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-NH.sub.2                                                                   H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-NH.sub.2                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-NH.sub.2                                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NH.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-NH.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -2-NH.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-NH.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-NH.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.5 C.sub.6 H.sub.4 -3-NH.sub.2                                                           H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NH.sub.2                                                   H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-NH.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -2-NH.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-NH.sub.2                                                          H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-NH.sub.2                                              H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-NH.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-NH.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-NH.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-NH.sub.2                                        H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-NH.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-NH.sub.2                                           H      H    H   H                                    (CH.sub.2).sub.3 CH (CH.sub.2).sub.6 C CC.sub.2 H.sub.5 !C.sub.6 H.sub.4      -4-NH.sub.2              H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NH.sub.2                                              H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-NH.sub.2                                                          H      H    H   H                                    CH.sub.2 CH(C.sub.7 H.sub.15)C.sub.6 H.sub.10 -4-NH.sub.2                                              H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-NH.sub.2                                              H      H    H   H                                    C.sub.6 H.sub.4 -4-NO.sub.2                                                                            H      H    H   H                                    C.sub.6 H.sub.10 -4-NO.sub.2                                                                           H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-NO.sub.2                                                                   H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-NO.sub.2                                                                  H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-NO.sub.2                                                                   H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NO.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NO.sub.2                                                           COCH.sub.3                                                                           H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-NO.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-NO.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-NO.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NO.sub.2                                               H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-NO.sub.2                                                   H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-NO.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-NO.sub.2                                                          H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-NO.sub.2                                              H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-NO.sub.2                                                           H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-NO.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-NO.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-NO.sub.2                                        H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-NO.sub.2                                                          H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-NO.sub.2                                           H      H    H   H                                    (CH.sub.2).sub.3 CH (CH.sub.2).sub.6 C CC.sub.2 H.sub.5 !C.sub.6 H.sub.4      -4-NO.sub.2              H      H    H   H                                    (CH.sub.2).sub.14 C CC.sub.6 H.sub.4 -3-NO.sub.2                                                       H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-NO.sub.2                                                          H      H    H   H                                    CH.sub.2 CH(C.sub.7 H.sub.15)C.sub.6 H.sub.10 -4-NO.sub.2                                              H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-NO.sub.2                                              H      H    H   H                                    C.sub.6 H.sub.4 -4-OH    H      H    H   H                                    C.sub.6 H.sub.10 -4-OH   H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OH                                                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OH                                                                         COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.10 -4-OH                                                                        H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-OH                                                                         H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OH                                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OH                                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-OH                                                                H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-OH                                                                 H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-OH                                                     H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-OH                                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-OH                                                                 H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-OH                                                                H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-OH                                                    H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -2-OH                                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-OH                                                                 H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-OH                                                                H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-OH                                                                H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-OH                                              H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-OH                                                                H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-OH                                                 H      H    H   H                                    (CH.sub.2).sub.3 CH (CH.sub.2).sub.6 C CC.sub.2 H.sub.5 !C.sub.6 H.sub.4      -4-OH                    H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -3-OH                                                    H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-OH                                                                H      H    H   H                                    CH.sub.2 CH(C.sub.7 H.sub.15)C.sub.6 H.sub.10 -4-OH                                                    H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-OH                                                    H      H    H   H                                    C.sub.6 H.sub.4 -4-COOH  H      H    H   H                                    C.sub.6 H.sub.10 -4-COOH H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-COOH                                                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-COOH                                                                      H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -3-COOH                                                                       H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-COOH                                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-COOH                                                               H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-COOH                                                              H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-COOH                                                               H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.4 -3-COOH                                                   H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -2-COOH                                                       H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-COOH                                                       H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-COOH                                                               H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -2-COOH                                                              H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -3-COOH                                                              H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-COOH                                                              H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-COOH                                                  H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-COOH                                                               H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-COOH                                                              H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-COOH                                                              H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-COOH                                            H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-COOH                                                              H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-COOH                                               H      H    H   H                                    (CH.sub.2).sub.3 CH (CH.sub.2).sub.6 C CC.sub.2 H.sub.5 !C.sub.6 H.sub.4      -4-COOH                  H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -3-COOH                                                  H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-COOH                                                              H      H    H   H                                    CH.sub.2 CH(C.sub.7 H.sub.15)C.sub.6 H.sub.10 -4-COOH                                                  H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-COOH                                                  H      H    H   H                                    C.sub.6 H.sub.4 -4-Br    H      H    H   H                                    C.sub.6 H.sub.10 -4-Cl   H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-Br                                                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.10 -4-Cl                                                                        H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-Cl                                                                         H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-F                                                                          H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-F                                                                          COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -3-F                                                                          H      H    H   H                                    (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-Br                                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-F                                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Cl                                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Cl                                                                 COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Br                                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Br                                                                 COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-I                                                                  H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -2-Br                                                                H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.10 -4-Br                                                                H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-F                                                                  H      H    H   H                                    (CH.sub.2).sub.3 CH(C.sub.3 H.sub.7)C.sub.6 H.sub.4 -2-Br                                              H      H    H   H                                    (CH.sub.2).sub.3 CH(C.sub.3 H.sub.7)C.sub.6 H.sub.4 -3-Br                                              H      H    H   H                                    CHCHCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.4 -3-Br                                                         H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-F                                                                  H      H    H   H                                    (CH.sub.2).sub.7 C.sub.6 H.sub.10 -4-Br                                                                H      H    H   H                                    CH.sub.2 C C(CH.sub.2).sub.4 C.sub.6 H.sub.10 -4-Br                                                    H      H    H   H                                    (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-F                                                                  H      H    H   H                                    (CH.sub.2).sub.9 C.sub.8 H.sub.14 -4-F                                                                 H      H    H   H                                    (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-Br                                                                H      H    H   H                                    (CH.sub.2).sub.6 CH(C.sub.4 H.sub.9)C.sub.6 H.sub.4 -4-F                                               H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -2-Br                                                                H      H    H   H                                    (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-Br                                                                H      H    H   H                                    (CH.sub.2).sub.10 C CCH(CH.sub.3)C.sub.6 H.sub.4 -4-Cl                                                 H      H    H   H                                    (CH.sub.2).sub.3 CH (CH.sub.2).sub.6 C CC.sub.2 H.sub.5 !C.sub.6 H.sub.4      -4-Br                    H      H    H   H                                    (CH.sub.2).sub.14 CH(CH.sub.3)C.sub.6 H.sub.4 -3-Cl                                                    H      H    H   H                                    (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-Br                                                                H      H    H   H                                    CH.sub.2 CH(C.sub.7 H.sub.15)C.sub.6 H.sub.10 -4-F                                                     H      H    H   H                                    (CH.sub.2).sub.8 CH(CH.sub.3)C.sub.6 H.sub.10 -4-Cl                                                    H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.3 (-4-NH.sub.2)-3-Cl                                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.9 (-4-NH.sub.2)-2-CH.sub.3                                                      H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.3 (-2-NHCOCH.sub.3)-4-OCH.sub.3                                                 H      H    H   H                                    (CH.sub.2).sub.3 C.sub.6 H.sub.9 (-4-COOC.sub.2 H.sub.5)-3-C.sub.10           H.sub.21                 H      H    H   H                                    (CH.sub.2).sub.4 C.sub.6 H.sub.2 (-4-Br)(-3-C.sub.2 H.sub.5)-2-COOH                                    H      H    H   H                                    (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.2 (-3-C.sub.4 H.sub.9 (-2-F)-4-    NO.sub.2                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.3 (-3-F)-4-C.sub.8 H.sub.17                                                     H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.3 (-3-F)-4-C.sub.8 H.sub.17                                                     COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.3 (-2-C.sub.2 H.sub.5)-4-C.sub.8 H.sub.17                                       H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.3 (-2-C.sub.2 H.sub.5)-4-C.sub.8 H.sub.17                                       COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.3 (-3-CH.sub.3)-4-C.sub.8 H.sub.17                                              H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.3 (-3-CH.sub.3)-4-C.sub.8 H.sub.17                                              COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.3 (-4-OC.sub.7 H.sub.15)-3-OCH.sub.3                                            H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.3 (-4-OC.sub.7 H.sub.15)-3-OCH.sub.3                                            COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.3 (-4-OC.sub.7 H.sub.15)-3-CH.sub.3                                             H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.3 (-4-OC.sub.7 H.sub.15)-3-CH.sub.3                                             COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                            ##STR33##               H      H    H   H                                     ##STR34##               COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                            ##STR35##               H      H    H   H                                     ##STR36##               COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                            ##STR37##               H      H    H   H                                     ##STR38##               COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                            ##STR39##               H      H    H   H                                     ##STR40##               COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.6 COC.sub.6 H.sub.4 -4-C.sub.6 H.sub.13                                                 H      H    H   H                                    COC.sub.6 H.sub.4 -4-C.sub.7 H.sub.15                                                                  H      H    H   H                                    COC.sub.6 H.sub.4 -4-C.sub.7 H.sub.15                                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           COC.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                                  H      H    H   H                                    COC.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                                  COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH(OH)C.sub.6 H.sub.4 -4-C.sub.7 H.sub.15                                                              H      H    H   H                                    CH(OH)C.sub.6 H.sub.4 -4-C.sub.7 H.sub.15                                                              COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH(OH)C.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                              H      H    H   H                                    CH(OH)C.sub.6 H.sub.4 -4-C.sub.8 H.sub.17                                                              COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.5 OC.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                 H      H    H   H                                    (CH.sub.2).sub.5 OC.sub.6 H.sub.4 -4-OC.sub.6 H.sub.13                                                 COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 F                                                        H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 F                                                        COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 -4-OCF.sub.2 C.sub.6 H.sub.13                                                 H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 -4-OCF.sub.2 C.sub.6 H.sub.13                                                 COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.8 OC.sub.6 H.sub.5                                                                      H      H    H   H                                    (CH.sub.2).sub.8 OC.sub.6 H.sub.5                                                                      COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           (CH.sub.2).sub.11 OC.sub.6 H.sub.5                                                                     COCH.sub.3                                                                           H    H   H                                    (CH.sub.2).sub.11 OC.sub.6 H.sub.5                                                                     H      H    H   H                                    (CH.sub.2).sub.5 O(CH.sub.2).sub.2 OC.sub.6 H.sub.5                                                    H      H    H   H                                    (CH.sub.2).sub.5 O(CH.sub.2).sub.2 OC.sub.6 H.sub.5                                                    COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5                                                     H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5                                                     COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 O(CH.sub.2).sub.6 C.sub.6 H.sub.5                                             H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 O(CH.sub.2).sub.6 C.sub.6 H.sub.5                                             COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           CH.sub.2 C.sub.6 H.sub.4 CH.sub.2 O(CH.sub.2).sub.5 C.sub.6 H.sub.5                                    H      H    H   H                                    CH.sub.2 C.sub.6 H.sub.4 CH.sub.2 O(CH.sub.2).sub.5 C.sub.6 H.sub.5                                    COCH.sub.3                                                                           H    COCH.sub.3                                                                        COCH.sub.3                           __________________________________________________________________________

    __________________________________________________________________________     ##STR41##                                                                    R                                          R.sup.2                                                                         R.sup.3                                                                         R.sup.4                                                                         R.sup.5                      __________________________________________________________________________     ##STR42##                                 H H H H                             ##STR43##                                 H H H H                             ##STR44##                                 H H H H                             ##STR45##                                 H H H H                             ##STR46##                                 H H H H                             ##STR47##                                 H H H H                             ##STR48##                                 H H H H                             ##STR49##                                 H H H H                             ##STR50##                                 H H H H                             ##STR51##                                 H H H H                             ##STR52##                                 H H H H                             ##STR53##                                 H H H H                             ##STR54##                                 H H H H                            __________________________________________________________________________

    ______________________________________                                         ##STR55##                                                                    R                  R.sup.2 R.sup.3                                                                             R.sup.4                                                                             R.sup.5                                ______________________________________                                        C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.13 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.14 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-(CH.sub.2).sub.15 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -2-(CH.sub.2).sub.9 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -3-(CH.sub.2).sub.9 CH.sub.3                                                     H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.3 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.5 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.9 CH.sub.3                                                    H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.10 CH.sub.3                                                   H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.11 CH.sub.3                                                   H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.12 CH.sub.3                                                   H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.13 CH.sub.3                                                   H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.14 CH.sub.3                                                   H       H     H     H                                      C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.14 CH.sub.3                                                   H       H     H     H                                      C.sub.6 H.sub.4 -2-O(CH.sub.2).sub.9 F                                                           H       H     H     H                                      C.sub.6 H.sub.4 -3-O(CH.sub.2).sub.13 F                                                          H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(CH.sub.2).sub.5 CH.sub.3                                           H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(CH.sub.2).sub.6 CH.sub.3                                           H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(CH.sub.2).sub.8 CH.sub.3                                           H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(CH.sub.2).sub.9 CH.sub.3                                           H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(CH.sub.2).sub.10 CH.sub.3                                          H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(CH.sub.2).sub.11 CH.sub.3                                          H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(CH.sub.2).sub.12 CH.sub.3                                          H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(CH.sub.2).sub.13 CH.sub.3                                          H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.5 CH.sub.3                                        H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.6 CH.sub.3                                        H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.7 CH.sub.3                                        H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.7 CH.sub.3                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.8 CH.sub.3                                        H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.9 CH.sub.3                                        H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.10 CH.sub.3                                       H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.11 CH.sub.3                                       H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.12 CH.sub.3                                       H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.13 CH.sub.3                                       H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.5 CH.sub.3                                        H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.6 CH.sub.3                                 H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.7 CH.sub.3                                 H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.7 CH.sub.3                                 COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.8 CH.sub.3                                 H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.9 CH.sub.3                                 H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.10 CH.sub.3                                H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.11 CH.sub.3                                H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.12 CH.sub.3                                H       H     H     H                                      CH.sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.13 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-S(O)(CH.sub.2).sub.10 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.6 CH.sub.3                         H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-S(O).sub.2 (CH.sub.2).sub.10 CH.sub.3                        H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                                    H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                                    COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                                    COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                                   COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                   COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 CH.sub.3                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 CH.sub.3                                   COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.13 CH.sub.3                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.14 CH.sub.3                                   COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.12 CH.sub.3                                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.12 CH.sub.3                                  COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.13 CH.sub.3                                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.13 CH.sub.3                                  COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 F                                           H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 F                                           COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 F                                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 F                                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 F                                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 F                                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 F                                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 F                                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.11 F                                         H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.11 F                                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.4 CH.sub.3                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.5 CH.sub.3                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.6 CH.sub.3                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.7 CH.sub.3                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.7 CH.sub.3                                   COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.9 CH.sub.3                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.10 CH.sub.3                                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.11 CH.sub.3                                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.11 CH.sub.3                                  COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.12 CH.sub.3                                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.10 -4-(CH.sub.2).sub.13 CH.sub.3                                  H       H     H     H                                      (CH.sub.2).sub.11 C.sub.6 H.sub.5                                                                H       H     H     H                                      (CH.sub.2).sub.15 C.sub.6 H.sub.5                                                                H       H     H     H                                      (CH.sub.2).sub.17 C.sub.6 H.sub.5                                                                H       H     H     H                                      (CH.sub.2).sub.19 C.sub.6 H.sub.5                                                                H       H     H     H                                      (CH.sub.2).sub.8 C.sub.6 H.sub.4 -4-F                                                            H       H     H     H                                      (CH.sub.2).sub.9 C.sub.6 H.sub.4 -4-F                                                            H       H     H     H                                      (CH.sub.2).sub.10 C.sub.6 H.sub.4 -3-F                                                           H       H     H     H                                      (CH.sub.2).sub.10 C.sub.6 H.sub.4 -3-F                                                           COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.11 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.12 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.13 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.10 C.sub.6 H.sub.4 -4-F                                                           COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.14 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.15 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.16 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.17 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.18 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.19 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.20 C.sub.6 H.sub.4 -4-F                                                           H       H     H     H                                      (CH.sub.2).sub.6 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                               H       H     H     H                                      (CH.sub.2).sub.6 O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.8 OCH.sub.2 C.sub.6 H.sub.5                                                       H       H     H     H                                      (CH.sub.2).sub.8 OCH.sub.2 C.sub.6 H.sub.5                                                       COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OCH.sub.2 C.sub.6 H.sub.5                                    H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OCH.sub.2 C.sub.6 H.sub.5                                    COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.2 C.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.5 C.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 C.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 C.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.3 OC.sub.6 H.sub.5                           H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 OC.sub.6 H.sub.5                           H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.5 OC.sub.6 H.sub.5                           H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 OC.sub.6 H.sub.5                           H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 OC.sub.6 H.sub.5                           H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 OC.sub.6 H.sub.5                           H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 OC.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 OC.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 OC.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 OC.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 OC.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 OC.sub.6 H.sub.5                            H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.2 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.3 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.5 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.5 C.sub.6 H.sub.4         -4-F               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.4         -4-F               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-OCH.sub.2 C.sub.6 H.sub.4 -4-F                               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.2 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.3 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.5 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 C.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.3 OC.sub.6 H.sub.4        -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.4 OC.sub.6 H.sub.4        -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.5 OC.sub.6 H.sub.4        -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 OC.sub.6 H.sub.4        -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 OC.sub.6 H.sub.4        -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 OC.sub.6 H.sub.4        -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 OC.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 OC.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 OC.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 OC.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 OC.sub.6 H.sub.4         -4-F               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 OC.sub.6 H.sub.4         -4-F               H       H     H     H                                      CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                                      H       H     H     H                                      CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                                      H       H     H     H                                      CH.sub.2 CHFC.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                         H       H     H     H                                      CH.sub.2 CHFC.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 CHFC.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                                         H       H     H     H                                      CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                                      H       H     H     H                                      CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                                     H       H     H     H                                      CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                     H       H     H     H                                      CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                     COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 CH.sub.3                                     H       H     H     H                                      CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.13 CH.sub.3                                     H       H     H     H                                      CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                                         H       H     H     H                                      CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                                         H       H     H     H                                      CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                         H       H     H     H                                      CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                                         H       H     H     H                                      CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                                         H       H     H     H                                      CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                                        H       H     H     H                                      CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                        H       H     H     H                                      CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH(OH)CH(OH)C.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 CH.sub.3                                        H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.5                                                                   H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                                      H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                                      H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                                      COCH.sub.3                                                                            H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                      H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                      COCH.sub.3                                                                            H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                                      H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                                      H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                                     H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                     H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                     COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 CH.sub.3                                     H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.13 CH.sub.3                                     H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.5                              H       H     H     H                                       CH(OH)!.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.5                              H       H     H     H                                      CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.5                              H       H     H     H                                      CH(OH)CH.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.5                              COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                              CH(OH)!.sub.2 C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.5                              COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 CH(OH)C.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.5                              COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                                                 H       H     H     H                                      CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                                                 H       H     H     H                                      CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                                 H       H     H     H                                      CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                                 COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                                                 H       H     H     H                                      CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                                                 H       H     H     H                                      CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                                                H       H     H     H                                      CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                                H       H     H     H                                      CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 CH.sub.3                                                H       H     H     H                                      CHCHC.sub.6 H.sub.4 -4-(CH.sub.2).sub.13 CH.sub.3                                                H       H     H     H                                      CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 CH.sub.3                               H       H     H     H                                      CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                               H       H     H     H                                      CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                               H       H     H     H                                      CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                               H       H     H     H                                      CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                               H       H     H     H                                      CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                               H       H     H     H                                      CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                              H       H     H     H                                      CH.sub.2 CHCHCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                              H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                                           H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                                           H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                           H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 CH.sub.3                                           COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 CH.sub.3                                           H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 CH.sub.3                                           H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 CH.sub.3                                          H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                          H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.11 CH.sub.3                                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.12 CH.sub.3                                          H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.13 CH.sub.3                                          H       H     H     H                                      CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                               H       H     H     H                                      CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 OCH.sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 CH.sub.3                                  H       H     H     H                                      CH.sub.2 O(CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 CH.sub.3                          H       H     H     H                                      CH.sub.2 O(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 CH.sub.3                          H       H     H     H                                      CH.sub.2 O(CH.sub.2).sub.4 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 CH.sub.3                          H       H     H     H                                      CH.sub.2 O(CH.sub.2).sub.5 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 CH.sub.3                          H       H     H     H                                      CH.sub.2 O(CH.sub.2).sub.6 C.sub.6 H.sub.4 -4-CH.sub.2 CH.sub.3                                  H       H     H     H                                      CH.sub.2 O(CH.sub.2).sub.7 C.sub.6 H.sub.4 -4-CH.sub.3                                           H       H     H     H                                      CH.sub.2 O(CH.sub.2).sub.8 C.sub.6 H.sub.5                                                       H       H     H     H                                      CH.sub.2 O(CH.sub.2).sub.11 C.sub.6 H.sub.5                                                      H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 C.sub.6 H.sub.5                                    H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 C.sub.6 H.sub.5                                    H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 C.sub.6 H.sub.5                                    H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 C.sub.6 H.sub.5                                    COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             CH.sub.2 OC.sub.6 H.sub.4 -4-O(CH.sub.2).sub.6 C.sub.6 H.sub.4 -4-F                              H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-O(CH.sub.2).sub.7 C.sub.6 H.sub.5                                   H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-O(CH.sub.2).sub.8 C.sub.6 H.sub.5                                   H       H     H     H                                      CH.sub.2 OC.sub.6 H.sub.4 -4-O(CH.sub.2).sub.9 C.sub.6 H.sub.5                                   H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.3 (3-OCH.sub.3)-4-OCH.sub.11 H.sub.23                             H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.3 (3-OCH.sub.3)-4-OCH.sub.11 H.sub.23                             COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.3 (2-F)-4-(CH.sub.2).sub.7 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.3 (2-F)-4-(CH.sub.2).sub.7 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.3 (2-F)-4-(CH.sub.2).sub.11 CH.sub.3                              H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.3 (2-F)-4-(CH.sub.2).sub.11 CH.sub.3                              COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.3 (3-F)-4-O(CH.sub.2).sub.6 CH.sub.3                              H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.3 (3-F)-4-O(CH.sub.2).sub.6 CH.sub.3                              COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.3 (3-F)-4-O(CH.sub.2).sub.10 CH.sub.3                             H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.3 (3-F)-4-O(CH.sub.2).sub.10 CH.sub.3                             COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.3 (2-F)-4-O(CH.sub.2).sub.6 CH.sub.3                              H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.3 (2-F)-4-O(CH.sub.2).sub.6 CH.sub.3                              COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.3 (2-F)-4-O(CH.sub.2).sub.10 CH.sub.3                             H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.3 (2-F)-4-O(CH.sub.2).sub.10 CH.sub.3                             COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-N(CH.sub.3)C.sub.7 H.sub.15                                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-N(CH.sub.3)C.sub.7 H.sub.15                                  COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-N(CH.sub.3)C.sub.11 H.sub.23                                 H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-N(CH.sub.3)C.sub.11 H.sub.23                                 COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOC.sub.6 H.sub.13                                         H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOC.sub.6 H.sub.13                                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOC.sub.10 H.sub.21                                        H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-NHCOC.sub.10 H.sub.21                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             ______________________________________                                    

    ______________________________________                                         ##STR56##                                                                    R                  R.sup.2 R.sup.3                                                                             R.sup.4                                                                             R.sup.5                                ______________________________________                                        2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 CH.sub.3                                                 H       H     H     H                                      CH.sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                        H       H     H     H                                      CH.sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.3 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.6 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.5 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.5 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.5 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.6 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.4 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.7 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.3 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.8 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.9 -2-C.sub.4 H.sub.2 S-4-CH.sub.2 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.9 -2-C.sub.4 H.sub.2 S-4-CH.sub.2 CH.sub.3                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.10 -2-C.sub.4 H.sub.2 S-4-CH.sub.3                                                H       H     H     H                                      (CH.sub.2).sub.10 -2-C.sub.4 H.sub.2 S-4-CH.sub.3                                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.11 -2-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.12 -2-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.13 -2-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.13 -2-C.sub.4 H.sub.3 S                                                           COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.14 -2-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.15 -2-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.15 -2-C.sub.4 H.sub.3 S                                                           COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.16 -2-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.17 -2-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.18 -2-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.18 -2-C.sub.4 H.sub.3 S                                                           COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.11 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.11 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.12 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.12 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 C.sub.6                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 -2-C.sub.4 H.sub.3 S                                H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 -2-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 -2-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 -2-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 -2-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -2-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -2-C.sub.4 H.sub.3                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -2-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -2-C.sub.4 H.sub.3                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -2-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -2-C.sub.4 H.sub.3                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -2-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -2-C.sub.4 H.sub.3                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -2-C.sub.4 H.sub.3      S                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -2-C.sub.4 H.sub.3      S                  COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 -3-C.sub.4 H.sub.3 S                                H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 -3-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 -3-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 -3-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 -3-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -3-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -3-C.sub.4 H.sub.3                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -3-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -3-C.sub.4 H.sub.3                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -3-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -3-C.sub.4 H.sub.3                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -3-C.sub.4 H.sub.3                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -3-C.sub.4 H.sub.3                          COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -3-C.sub.4 H.sub.3      S                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -3-C.sub.4 H.sub.3      S                  COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 CH.sub.3                                                  H       H     H     H                                      CH.sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 CH.sub.3                                        H       H     H     H                                      CH.sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 CH.sub.3                                        COCH.sub.3                                                                            H     H     H                                      CH.sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 CH.sub.3                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.3 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.3 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.6 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.4 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.4 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.5 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.4 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.6 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.3 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.7 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -2-C.sub.4 H.sub.2 S-5-CH.sub.2 CH.sub.3                                        COCH.sub.3                                                                            H     H     H                                      (CH.sub.2).sub.7 -2-C.sub.4 H.sub.2 S-5-CH.sub.2 CH.sub.3                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.8 -2-C.sub.4 H.sub.2 S-5-CH.sub.3                                                 H       H     H     H                                      (CH.sub.2).sub.8 -2-C.sub.4 H.sub.2 S-5-CH.sub.3                                                 COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.8 -3-C.sub.4 H.sub.3 S                                                            H       H     H     H                                      (CH.sub.2).sub.9 -3-C.sub.4 H.sub.3 S                                                            H       H     H     H                                      (CH.sub.2).sub.10 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.11 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.12 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.13 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.14 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.15 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.16 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.17 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.18 -3-C.sub.4 H.sub.3 S                                                           H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.12 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.12 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 C.sub.6                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.11 CH.sub.3                                                 H       H     H     H                                      CH.sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 CH.sub.3                                       H       H     H     H                                      CH.sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 CH.sub.3                                       COCH.sub.3                                                                            H     H     H                                      CH.sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 CH.sub.3                                       COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                COCH.sub.3                                                                            H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.3 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.3 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.4 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.7 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.5 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.6 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.6 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.5 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.5 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.7 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.4 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.8 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.8 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.3 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.9 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.10 -3-C.sub.4 H.sub.2 S-4-CH.sub.2 CH.sub.3                                       COCH.sub.3                                                                            H     H     H                                      (CH.sub.2).sub.10 -3-C.sub.4 H.sub.2 S-4-CH.sub.2 CH.sub.3                                       COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.11 -3-C.sub.4 H.sub.2 S-4-CH.sub.3                                                H       H     H     H                                      (CH.sub.2).sub.11 -3-C.sub.4 H.sub.2 S-4-CH.sub.3                                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.11 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.11 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.12 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.12 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-4-(CH.sub.2).sub.10 C.sub.6                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 CH.sub.3                                                 H       H     H     H                                      CH.sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 CH.sub.3                                        H       H     H     H                                      CH.sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 CH.sub.3                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.3 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.6 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.5 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.5 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.5 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.6 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.4 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.7 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.3 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.8 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.9 -3-C.sub.4 H.sub.2 S-5-CH.sub.2 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.9 -3-C.sub.4 H.sub.2 S-5-CH.sub.2 CH.sub.3                                        COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.10 -3-C.sub.4 H.sub.2 S-5-CH.sub.3                                                H       H     H     H                                      (CH.sub.2).sub.10 -3-C.sub.4 H.sub.2 S-5-CH.sub.3                                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 CH.sub.3                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.11 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.11 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.12 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.12 CH.sub.3                               COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.4 H.sub.2 S-5-(CH.sub.2).sub.10 C.sub.6                                COCH.sub.3                                                                            H     COCH.sub.3                                                                          COCH.sub.3                             ______________________________________                                    

    ______________________________________                                         ##STR57##                                                                    R                  R.sup.2 R.sup.3                                                                             R.sup.4                                                                             R.sup.5                                ______________________________________                                        2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.10 CH.sub.3                                                 H       H     H     H                                      CH.sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.9 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.3 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.5 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.8 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.9 -2-C.sub.5 H.sub.3 N-4-CH.sub.2 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.10 -2-C.sub.5 H.sub.3 N-4-CH.sub.3                                                H       H     H     H                                      CH.sub.2 -2-C.sub.5 H.sub.4 N                                                                    H       H     H     H                                      CH.sub.2 -2-C.sub.5 H.sub.4 N                                                                    CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.11 -2-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.11 -2-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.9 -2-C.sub.5 H.sub.4 N                                                            H       H     H     H                                      (CH.sub.2).sub.9 -2-C.sub.5 H.sub.4 N                                                            CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.10 -2-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.10 -2-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.12 -2-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.12 -2-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.13 -2-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.13 -2-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.14 -2-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.14 -2-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.15 -2-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.15 -2-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.16 -2-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.16 -2-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.17 -2-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.17 -2-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.8 CH.sub.3                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.12 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.12 CH.sub.3                               CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-CH.sub.2 C.sub.6 H.sub.5                                 CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-4-(CH.sub.2).sub.10 C.sub.6                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 -2-C.sub.5 H.sub.4 N                                H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 -2-C.sub.5 H.sub.4 N                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 -2-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 -2-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 -2-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 -2-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 -2-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 -2-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 -2-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 -2-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -2-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -2-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -2-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -2-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -2-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -2-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -2-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -2-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -2-C.sub.5 H.sub.4      N                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -2-C.sub.5 H.sub.4      N                  CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.10 CH.sub.3                                                 H       H     H     H                                      CH.sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.9 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.3 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.5 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.8 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.9 -4-C.sub.5 H.sub.3 N-2-CH.sub.2 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.10 -4-C.sub.5 H.sub.3 N-2-CH.sub.3                                                H       H     H     H                                      CH.sub.2 -4-C.sub.5 H.sub.4 N                                                                    H       H     H     H                                      CH.sub.2 -4-C.sub.5 H.sub.4 N                                                                    CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.11 -4-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.11 -4-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.9 -4-C.sub.5 H.sub.4 N                                                            H       H     H     H                                      (CH.sub.2).sub.9 -4-C.sub.5 H.sub.4 N                                                            CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.10 -4-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.10 -4-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.12 -4-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.12 -4-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.13 -4-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.13 -4-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.14 -4-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.14 -4-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.15 -4-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.15 -4-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.16 -4-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.16 -4-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.17 -4-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.17 -4-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.8 CH.sub.3                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.12 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.12 CH.sub.3                               CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-CH.sub.2 C.sub.6 H.sub.5                                 CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -4-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.10 C.sub.6                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 -4-C.sub.5 H.sub.4 N                                H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 -4-C.sub.5 H.sub.4 N                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 -4-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 -4-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 -4-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 -4-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 -4-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 -4-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 -4-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 -4-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -4-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -4-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -4-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -4-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -4-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -4-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -4-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -4-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -4-C.sub.5 H.sub.4      N                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -4-C.sub.5 H.sub.4      N                  CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.9 CH.sub.3                                                  H       H     H     H                                      CH.sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.3 CH.sub.3                                        H       H     H     H                                      CH.sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.8 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.3 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.5 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.8 -2-C.sub.5 H.sub.3 N-5-CH.sub.2 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.9 -2-C.sub.5 H.sub.3 N-5-CH.sub.3                                                 H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 CH.sub.3                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.11 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.11 CH.sub.3                               CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-CH.sub.2 C.sub.6 H.sub.5                                 CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.10 C.sub.6                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.9 CH.sub.3                                                  H       H     H     H                                      CH.sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.3 CH.sub.3                                        H       H     H     H                                      CH.sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.8 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.3 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -5-C.sub.5 H.sub.3 N-25-(CH.sub.2).sub.5 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.5 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.8 -5-C.sub.5 H.sub.3 N-2-CH.sub.2 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.9 -5-C.sub.5 H.sub.3 N-2-CH.sub.3                                                 H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.7 CH.sub.3                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.11 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.11 CH.sub.3                               CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-CH.sub.2 C.sub.6 H.sub.5                                 CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -5-C.sub.5 H.sub.3 N-2-(CH.sub.2).sub.10 C.sub.6                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.10 CH.sub.3                                                 H       H     H     H                                      CH.sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.9 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.3 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.5 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.8 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.9 -2-C.sub.5 H.sub.3 N-6-CH.sub.2 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.10 -2-C.sub.5 H.sub.3 N-6-CH.sub.3                                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.8 CH.sub.3                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.12 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.12 CH.sub.3                               CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-CH.sub.2 C.sub.6 H.sub.5                                 CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -2-C.sub.5 H.sub.3 N-6-(CH.sub.2).sub.10 C.sub.6                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.10 CH.sub.3                                                 H       H     H     H                                      CH.sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.9 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.3 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.4 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.6 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.5 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.5 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.6 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.4 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.7 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.3 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.8 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.2 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.9 -3-C.sub.5 H.sub.3 N-5-CH.sub.2 CH.sub.3                                        H       H     H     H                                      (CH.sub.2).sub.10 -3-C.sub.5 H.sub.3 N-5-CH.sub.3                                                H       H     H     H                                      (CH.sub.2).sub.11 -3-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.11 -3-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.9 -3-C.sub.5 H.sub.4 N                                                            H       H     H     H                                      (CH.sub.2).sub.9 -3-C.sub.5 H.sub.4 N                                                            CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.10 -3-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.10 -3-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.12 -3-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.12 -3-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.13 -3-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.13 -3-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.14 -3-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.14 -3-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.15 -3-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.15 -3-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.16 -3-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.16 -3-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.17 -3-C.sub.5 H.sub.4 N                                                           H       H     H     H                                      (CH.sub.2).sub.17 -3-C.sub.5 H.sub.4 N                                                           CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.8 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.8 CH.sub.3                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.12 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.12 CH.sub.3                               CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-CH.sub.2 C.sub.6 H.sub.5                                 H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 CH.sub.3                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 CH.sub.3                                H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.11 CH.sub.3                               CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.11 CH.sub.3                               H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-CH.sub.2 C.sub.6 H.sub.5                                 CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.2 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.3 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.4 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.5 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.6 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.7 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.8 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         H       H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.9 C.sub.6 H.sub.5                         CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.10 C.sub.6                                H.sub.5 H     H     H                                      (CH.sub.2).sub.2 -3-C.sub.5 H.sub.3 N-5-(CH.sub.2).sub.10 C.sub.6                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 -3-C.sub.5 H.sub.4 N                                H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-CH.sub.2 -3-C.sub.5 H.sub.4 N                                CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 -3-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.2 -3-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 -3-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.3 -3-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 -3-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.4 -3-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 -3-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.5 -3-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -3-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.6 -3-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -3-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.7 -3-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -3-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.8 -3-C.sub.5 H.sub.4                          CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.9 -3-C.sub.5 H.sub.4                          H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 (CH.sub.2).sub.9 -3-C.sub.5 H.sub.4                             CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -3-C.sub.5 H.sub.4      N                  H       H     H     H                                      (CH.sub.2).sub.2 C.sub.6 H.sub.4 -4-(CH.sub.2).sub.10 -3-C.sub.5 H.sub.4      N                  CH.sub.3 CO                                                                           H     CH.sub.3 CO                                                                         CH.sub.3 CO                            ______________________________________                                    

    __________________________________________________________________________     ##STR58##                                                                    R                     R.sup.2                                                                           R.sup.3                                                                          R.sup.4                                                                           R.sup.5                                      __________________________________________________________________________     ##STR59##            H   H  H   H                                             ##STR60##            H   H  H   H                                             ##STR61##            H   H  H   H                                             ##STR62##            H   H  H   H                                             ##STR63##            H   H  H   H                                             ##STR64##            H   H  H   H                           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             H  CH.sub.3 CO                                                                       CH.sub.3 CO                                   ##STR239##           H   H  H   H                                             ##STR240##           H   H  H   H                                             ##STR241##           H   H  H   H                                             ##STR242##           H   H  H   H                                             ##STR243##           CH.sub.3 CO                                                                       H  CH.sub.3 CO                                                                       CH.sub.3 CO                                   ##STR244##           H   H  H   H                                             ##STR245##           H   H  H   H                                             ##STR246##           H   H  H   H                                            __________________________________________________________________________

    ______________________________________                                         ##STR247##                                                                   R                      R.sup.2                                                                             R.sup.3                                                                              R.sup.4                                                                           R.sup.5                               ______________________________________                                         ##STR248##            H     H      H   H                                      ##STR249##            H     H      H   H                                      ##STR250##            H     H      H   H                                      ##STR251##            H     H      H   H                                      ##STR252##            H     H      H   H                                      ##STR253##            H     H      H   H                    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##STR382##            H     H      H   H                                      ##STR383##            H     H      H   H                                      ##STR384##            H     H      H   H                                      ##STR385##            H     H      H   H                                      ##STR386##            H     H      H   H                                      ##STR387##            H     H      H   H                                      ##STR388##            H     H      H   H                                      ##STR389##            H     H      H   H                                     ______________________________________                                    

Examples of the pharmaceutically acceptable salts of the compounds ofthe formula (I) hereinafter referred to as Compound (I)! include saltswith inorganic acids, such as hydrochloride, hydrobromide and sulfate,salts with organic acids, such as acetate, fumarate, maleate, benzoate,citrate, malate, methanesulfonate and benzenesulfonate, and whencarboxyl group is included, salts with metals such as sodium salt,potassium salt, calcium salt and aluminum salt, salts with amines, suchas triethylamine and salts with dibasic amino acids, such as lysine. Thecompounds of the present invention encompass hydrates and solvates.

When the compounds of the present invention include geometric isomers,the present invention encompasses cis-compounds, trans-compounds andmixtures thereof. When the compounds of the present invention have oneor more asymmetric centers in the molecule, various optical isomers areobtained. The present invention also encompasses optical isomers,racemates, diastereomers and mixtures thereof.

The compounds of the present invention can be produced by the followingmethods.

(method A)

A compound of the formula (II)

    R.sup.1 CH.sub.2 --G                                       (II)

wherein R¹ CH₂ is the same as the aforementioned R¹ CH₂, R¹ aCH₂, R¹bCH₂, Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, Rl, Rm, Rn or Ro whichare encompassed in R, and G is a leaving group in wide use in the fieldof organic synthetic chemistry, such as halogen (fluorine, chlorine,bromine, iodine), methanesulfonyloxy, p-toluenesulfonyloxy ortrifluoromethanesulfonyloxy hereinafter referred to as Compound (II)!,or where R¹ has a functional group (e.g. amino, hydroxyl group,mercapto, ketone, carboxyl), a compound with protection of thefunctional group as necessary hereinafter referred to as CompoundB-(II)! is condensed, in the presence of a base, with a compound of theformula (III) ##STR390## wherein Y is lower alkyl (e.g. methyl, ethyl,propyl, isopropyl, butyl, tert-butyl) or aralkyl (e.g. benzyl,nitrobenzyl, methoxybenzyl, methylbenzyl), and Q is an amino-protectinggroup widely used in the field of organic synthetic chemistry, such asacetyl, benzoyl, tert-butoxycarbonyl or benzyloxycarbonyl, where the twoYs in the molecule in the formula may together form a ring such asdioxane and Q and Y in the molecule may together form a ring such asoxazolidine or oxazine hereinafter referred to as Compound (III)! togive a compound of the formula (IV) ##STR391## wherein R¹, Q and Y areas defined above hereinafter referred to as Compound (IV)!, which issubjected to reduction of carboxyl with a suitable reducing agent anddeprotection as necessary to give a compound of the formula (I-29)##STR392## wherein R¹ is as defined above hereinafter referred to asCompound (I-29)! or an N- and/or O-protected compound thereof.

Examples of the base to be used in the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the organic solvent to be used in the condensation includemethanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (IV) can be purified by a method known in the field of organicsynthetic chemistry, such as solvent extraction, recrystallization,chromatography and a method using an ion exchange resin.

Examples of the reducing agent to be used in the reduction of carboxylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used in the reduction of carboxylinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The temperature for the reduction of carboxyl is generally from -20° C.to 80° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The reduction of carboxyl is generally carried out for 30 minutes to 10hours and the reaction period longer or shorter than the indicatedperiod may be used as necessary.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the objective compoundcan be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyand a method using an ion exchange resin.

(Method B)

A Compound (II) or a Compound B-(II) is condensed, in the presence of abase, with a compound of the formula (V) ##STR393## wherein Y and Q areas defined above, and Z is a hydroxy-protecting group widely used in thefield of organic synthetic chemistry, such as acetyl, benzoyl, benzyl,trimethylsilyl, tert-butyldimethylsilyl, methoxymethyl,methoxyethoxymethyl or tetrahydropyranyl hereinafter referred to asCompound (V)! to give a Compound of the formula (VI) ##STR394## whereinR¹, Q, Y and Z are as defined above hereinafter referred to as Compound(VI)!. The obtained compound is then subjected to reduction of carboxylwith a suitable reducing agent and deprotection as necessary to give acompound (I-29) or an N- and/or O-protected compound thereof.

Examples of the base to be used in the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the organic solvent to be used in the condensation includemethanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (VI) can be purified by a method known in the field of organicsynthetic chemistry, such as solvent extraction, recrystallization,chromatography and a method using an ion exchange resin.

Examples of the reducing agent to be used for the reduction of carboxylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used for the reduction of carboxylinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The temperature of the reduction of carboxyl is generally from -20° C.to 80° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The reduction of carboxyl is generally carried out for 30 minutes to 10hours and the reaction period longer or shorter than the indicatedperiod may be used as necessary.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the objective compoundcan be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyand a method using an ion exchange resin.

(Method C)

A Compound (II) or a Compound B-(II) is condensed, in the presence of abase, with a compound of the formula (VII) ##STR395## wherein Y is asdefined above hereinafter referred to as Compound (VlI)! to give acompound of the formula (VIII) ##STR396## wherein R¹ and Y are asdefined above hereinafter referred to as Compound (VIII)!. The obtainedcompound is then subjected to reduction of carboxyl and azide with asuitable reducing agent and deprotection as necessary to give a Compound(I-29) or an O-protected compound thereof.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the organic solvent to be used for the condensation includemethanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (VIII) can be purified by a method known in the field oforganic synthetic chemistry, such as solvent extraction,recrystallization, chromatography and a method using an ion exchangeresin.

Examples of the reducing agent to be used for the reduction of carboxylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used for the reduction of carboxylinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The temperature of the reduction of carboxyl is generally from -20° C.to 80° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The reduction is generally carried out for 30 minutes to 10 hours andthe reaction period longer or shorter than the indicated period may beused as necessary.

Examples of the reducing agent to be used for the reduction of azideinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and transition metal such aspalladium-carbon, platinum oxide, Raney nickel, rhodium or ruthenium forcatalytic reduction.

Examples of the organic solvent to be used for the reduction of azideinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether, dioxane, acetone, ethyl acetate, acetic acid, benzene, toluene,xylene, dimethylformamide and dimethyl sulfoxide.

The temperature of the reduction of azide is generally from -20° C. to80° C. and a temperature lower or higher than this temperature range maybe selected on demand.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the objective compoundcan be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyand a method using an ion exchange resin.

(Method D)

A Compound (II) or a Compound B-(II) is condensed, in the presence of abase, with a compound of the formula (IX) ##STR397## wherein Z¹ and Z²are the same or different and each is hydroxyl-protecting group widelyused in the field of organic synthetic chemistry, such as acetyl,benzoyl, benzyl, trimethylsilyl, tert-butyldimethylsilyl, methoxymethyl,methoxyethoxymethyl or tetrahydropyranyl and Z¹ and Z² may together forma ring such as dioxane hereinafter referred to as Compound (IX)! to givea compound of the formula (X) ##STR398## wherein R¹, Z¹ and Z² are asdefined above hereinafter referred to as Compound (X)!. The obtainedcompound is then subjected to reduction of nitro with a suitablereducing agent and deprotection as necessary to give a Compound (I-29)or an O-protected compound thereof.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the organic solvent to be used for the condensation includemethanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (X) can be purified by a method known in the field of organicsynthetic chemistry, such as solvent extraction, recrystallization,chromatography and a method using an ion exchange resin.

Examples of the reducing agent to be used for the reduction of nitroinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, transition metal such aspalladium-carbon, platinum oxide, Raney nickel, rhodium or ruthenium forcatalytic reduction, and metal such as iron, zinc or tin.

Examples of the solvent to be used for the reduction of nitro includewater, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether, dioxane, acetone, ethyl acetate, acetic acid, benzene, toluene,xylene, dimethylformamide and dimethyl sulfoxide.

The reduction of nitro generally proceeds at a temperature of from -20°C. to 80° C. and a temperature lower or higher than this temperaturerange may be selected on demand.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the objective compoundcan be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyand a method using an ion exchange resin.

The above-mentioned methods A through D can be used for the synthesis ofthe compounds of the formulas (I-1) to (I-18)

(Method E)

A compound of the formula (XI)

    (R.sup.11).sub.n --M                                       (XI)

wherein R¹¹ is the same as the aforementioned CH₂ R¹, CH₂ R¹ a, CH₂ R¹b, Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, Rl, Rm, Rn, Ro, Rp, Rq,CH═CHRt, CH═CHRu, (CH₂)α--X--(CH₂)βRv (when α≧1) or CH₂ ORw which areencompassed in R, M is a metal in wide use in the field of organicsynthetic chemistry, such as lithium, magnesium chloride, magnesiumbromide, magnesium iodide, copper, lithium copper or nickel, and n is aninteger of 1 to 3 hereinafter referred to as Compound (XI)!, or when R¹¹has a functional group (e.g. amino, hydroxyl group, mercapto, ketone,carboxy), a compound with protection of the functional group asnecessary hereinafter referred to as Compound B-(XI)! is subjected tonucleophilic addition to a compound of the formula (XII) ##STR399##wherein Y is as defined above and Q¹ is an imino-protecting group inwide use in the field of organic synthetic chemistry, such as acetyl,benzoyl, tert-butoxycarbonyl or benzyloxycarbonyl hereinafter referredto as Compound (XII)! to give a compound of the formula (IV-a)##STR400## wherein R¹¹, Q¹ and Y are as defined above hereinafterreferred to as Compound (IV-a)!. The obtained compound is then subjectedto reduction of carboxyl with a suitable reducing agent and deprotectionas necessary to give a compound of the formula (I-30) ##STR401## whereinR¹¹ is as defined above hereinafter referred to as Compound (I-30)! oran N- and/or O-protected compound thereof.

Examples of the organic solvent to be used for the addition includetetrahydrofuran, diethyl ether, ethylene glycol dimethyl ether,dimethylformamide, dimethyl sulfoxide, benzene, toluene, xylene,dioxane, methylene chloride, chloroform, dichloroethane andacetonitrile.

The addition generally proceeds at a temperature of from -100° C. to 80°C. and a temperature lower or higher than this temperature range may beselected on demand.

The addition is generally carried out for 30 minutes to 2 days and thereaction period longer or shorter than the indicated period may be usedas necessary.

After the addition is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (IV-a)can be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyand a method using an ion exchange resin.

Examples of the reducing agent to be used for the reduction of carboxylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used for the reduction of carboxylinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The reduction of carboxyl generally proceeds at a temperature of from-20° C. to 80° C. and a temperature lower or higher than thistemperature range may be selected on demand.

The reduction of carboxyl is generally carried out for 30 minutes to 10hours and the reaction period longer or shorter than the indicatedperiod may be used as necessary.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the objective compoundcan be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyand a method using an ion exchange resin.

The instant method can be used for the synthesis of the compounds of theformulas (I-1) to (I-20), (I-24), (I-25), (I-26) when α≧1 and (I-27).

(Method F)

A compound of the formula (XIII) ##STR402## wherein Hal is halogen suchas chlorine, bromine or iodine and Rt and Ru are as defined abovehereinafter referred to as Compound (XIII-1) or Compound (XIII-2)!, orwhen Rt and Ru have a functional group (e.g. amino, hydroxyl, mercapto,ketone, carboxyl), a compound with protection of the functional group asnecessary hereinafter referred to as Compound B-(XIII-1) or CompoundB-(XIII-2)! is condensed, in the presence of a base, with a compound ofthe formula (XIV) ##STR403## wherein Q¹ and Q² are amino-protectinggroups widely used in the field of organic synthetic chemistry, such asacetyl, benzoyl, tert-butoxycarbonyl, benzyloxycarbonyl or benzyl andone of them may be hydrogen, and Z¹ and Z² are as defined abovehereinafter referred to as Compound (XIV)! to give a compound of theformula (XV) ##STR404## wherein Rt, Ru, Q¹, Q², Z¹ and Z² are as definedabove hereinafter referred to as Compound (XV-1) or Compound (XV-2)!.The obtained compound is then subjected to deprotection as necessary togive a compound (I-24) or (I-25).

Examples of the base to be used in the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, potassium tert-butoxide,sodium hydride, potassium hydride, lithium diisopropylamide, butyllithium, lithium hexamethyldisilazane, triethylamine,diisopropylethylamine,-pyridine and 1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XV-1) or (XV-2) can be purified by a method known in the fieldof organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

The instant method can be used for the synthesis of the compounds of theformulas (I-24) and (I-25). By reducing the double bond of the compoundsof the formulas (I-24) and (I-25), or an N- and/or O-protected compoundthereof, the compounds of the formulas (I-1) through (I-18) and (I-26)when α≧2 can be obtained.

Examples of the reducing agent to be used for the reduction of thedouble bond include metal reducing reagent such as sodium borohydride,lithium borohydride or lithium aluminum hydride, and transition metalsuch as palladium-carbon, platinum oxide, Raney nickel, rhodium orruthenium for catalytic reduction.

Examples of the organic solvent to be used for the reduction of thedouble bond include methanol, ethanol, tert-butyl alcohol,tetrahydrofuran, diethyl ether, dioxane, acetone, ethyl acetate, aceticacid, benzene, toluene, xylene, dimethylformamide and dimethylsulfoxide.

The reduction of the double bond generally proceeds at a temperature offrom -20° C. to 80° C. and a temperature lower or higher than thistemperature range may be selected on demand.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the objectivecompounds of the formulas (I-1) through (I-18) and (I-26) when α≧2 canbe purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyor a method using an ion exchange resin.

(Method G)

A compound of the formula (XVI) ##STR405## wherein R¹¹¹ is theaforementioned CH₂ R¹, CH₂ R¹ a, CH₂ R¹ b, Ra, Rb, Rc, Rd, Re, Rf, Rg,Rh, Ri, Rj, Rk, Rl, Rm, Rn or Ro which are encompassed in R, and Rp, Rqand G are as defined above hereinafter referred to as Compound (XVI-1),Compound (XVI-2) or Compound (XVI-3)!, or when R¹¹¹, Rp and Rq have afunctional group (e.g. amino, hydroxyl, mercapto, ketone, carboxyl), acompound with protection thereof as necessary hereinafter referred to asCompound B-(XVI-1), Compound B-(XVI-2) or Compound B-(XVI-3)! is reactedwith a compound of the formula (XVII)

    M.sup.n+ (NO.sub.2.sup.-).sub.n                            (XVII)

wherein M is a metal such as sodium, potassium, magenesium, silver,calcium or lithium and n is an integer of 1 or 2 hereinafter referred toas Compound (XVII)! to give a compound of the formula (XVIII) ##STR406##wherein R¹¹¹, Rp and Rq are as defined above hereinafter referred to asCompound (XVIII-1), Compound (XVIII-2) or Compound (XVIII-3)!. Theobtained compound is condensed with formalin in the presence of a base,and then subjected to protection of hydroxyl as necessary to give acompound of the formula (XIX) ##STR407## wherein R¹¹¹, Rp, Rq, Z¹ and Z²are as defined above hereinafter referred to as Compound (XIX-1),Compound (XIX-2) or Compound (XIX-3)!. The obtained compound is thensubjected to reduction of nitro with a suitable reducing agent anddeprotection as necessary to give a desired compound inclusive of thecompounds (I-19) and (I-20).

Examples of the solvent to be used for the condensation of nitrite(XVII) and the Compound (XVI-1), (XVI-2) or (XVI-3) include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XVIII-1), (XVIII-2) or (XVIII-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

Examples of the solvent to be used for the condensation of the Compound(XVIII-1), (XVIII-2) or (XVIII-3) and formalin include water, methanol,ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether, ethyleneglycol dimethyl ether, dimethylformamide, dimethyl sulfoxide, benzene,toluene, xylene, dioxane, methylene chloride, chloroform, dichloroethaneand acetonitrile.

Examples of the base to be, used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XIX-1), (XIX-2) or (XIX-3) can be purified by a method knownin the field of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the reducing agent to be used for the reduction of nitroinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, transition metal such aspalladium-carbon, platinum oxide, Raney nickel, rhodium or ruthenium forcatalytic reduction, and metal such as iron, zinc or tin.

Examples of the solvent to be used for the reduction of nitro includewater, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether, dioxane, acetone, ethyl acetate, acetic acid, benzene, toluene,xylene, dimethylformamide and dimethyl sulfoxide.

The reduction of nitro generally proceeds at a temperature of from -20°C. to 80° C. and a temperature lower or higher than this temperaturerange may be selected on demand.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the objective compoundcan be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyor a method using an ion exchange resin.

The instant method is suitable for the synthesis of the compounds (I-19)and (I-20), as well as for the synthesis of the compounds of theformulas (I-1) through (I-18).

(Method H)

A compound of the formula (XX) ##STR408## wherein R¹, Rr and Rs are asdefined above hereinafter referred to as Compound (XX-1), Compound(XX-2) or Compound (XX-3)! is condensed, in the presence of a base, witha Compound (IX) and subjected to protection of hydroxyl as necessary togive a compound of the formula (XXI) ##STR409## wherein R¹, Rr, Rs, Z¹and Z² are as defined above and Za is hydrogen or a hydroxyl-protectinggroup in wide use in the field of organic synthetic chemistry, such asacetyl, benzoyl, benzyl, trimethylsilyl, tert-butyldimethylsilyl,methoxymethyl, methoxyethoxymethyl or tetrahydropyranyl hereinafterreferred to as Compound (XXI-1), Compound (XXI-2) or Compound (XXI-3)!.The obtained compound is then subjected to reduction of nitro with asuitable reducing agent and deprotection as necessary to give a compoundof the formula (XXII) ##STR410## wherein R¹, Rr and Rs are as definedabove hereinafter referred to as Compound (XXII-1), Compound (I-22) orCompound (I-23)!.

Examples of the-base to be used for the condensation with aldehydeinclude sodium hydroxide, sodium methoxide, sodium ethoxide, sodiumhydride, potassium hydride, lithium diisopropylamide, butyl lithium,lithium hexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXI-1), (XXI-2) or (XXI-3) can be purified by a method knownin the field of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the reducing agent to be used for the reduction of nitroinclude metal reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, transition metal such aspalladium-carbon, platinum oxide, Raney nickel, rhodium or ruthenium forcatalytic reduction, and metal such as iron, zinc or tin.

Examples of the solvent to be used for the reduction of nitro includewater, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether, dioxane, acetone, ethyl acetate, acetic acid, benzene, toluene,xylene, dimethylformamide and dimethyl sulfoxide.

The reduction of nitro generally proceeds at a temperature of from -20°C. to 80° C. and a temperature lower or higher than this temperaturerange may be selected on demand.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (XXII-1),(I-22) or (I-23) can be purified by a method known in the field oforganic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Accordingly, the instant method can be used for the synthesis of thecompounds of the formulas (I-21) through (I-23).

(Method I)

Compound (XVIII-1) can be also produced by the following method.

A compound of the formula (XX')

    R.sup.A CHO                                                (XX')

wherein R^(A) is a straight- or branched carbon chain optionally havinga substituent having a carbon number less 1 from that of the substituentat R¹¹¹ hereinafter referred to as Compound (XX')! is condensed withnitromethane in the presence of a base to give a compound of the formula(XXIII)

    R.sup.A CH═CHNO.sub.2                                  (XXIII)

wherein R^(A) is as defined above hereinafter referred to as Compound(XXIII)!. The obtained compound is then subjected to reduction of thedouble bond with a suitable reducing agent to give a compound (XVIII-1).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXIII) can be purified by a method known in the field oforganic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the reducing agent to be used for the reduction of thedouble bond include metallic reducing reagent such as lithiumborohydride or lithium aluminum hydride, and transition metal such aspalladium-carbon, platinum oxide, Raney nickel, rhodium or ruthenium forcatalytic reduction.

Examples of the organic solvent to be used for the reduction of thedouble bond include methanol, ethanol, tert-butyl alcohol,tetrahydrofuran, diethyl ether, dioxane, acetone, ethyl acetate, aceticacid, benzene, toluene, xylene, dimethylformamide and dimethylsulfoxide.

The reduction of the double bond generally proceeds at a temperature offrom -20° C. to 80° C. and a temperature lower or higher than thistemperature range may be selected on demand.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (XVIII-1)can be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyor a method using an ion exchange resin.

(Method J)

Compound (XXI-1), Compound (XXI-2) and Compound (XXI-3) can be alsoproduced by the following method.

A Compound (XX-1), (XX-2) or (XX-3) is condensed with nitromethane inthe presence of a base and subjected to protection of hydroxyl asnecessary to give a compound of the formula (XXIV) ##STR411## whereinR¹, Rr, Rs and Za are as defined above hereinafter referred to asCompound (XXIV-1), Compound (XXIV-2) or Compound (XXIV-3)!. The obtainedcompound is condensed with formalin in the presence of a base and thensubjected to protection of hydroxyl as necessary to give a Compound(XXI-1), (XXI-2) or (XXI-3).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXIV-1), (XXIV-2) or (XXIV-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

Examples of the solvent to be used for the condensation with formalininclude water, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran,diethyl ether, ethylene glycol dimethyl ether, dimethylformamide,dimethyl sulfoxide, benzene, toluene, xylene, dioxane, methylenechloride, chloroform, dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXI-1), (XXI-2) or (XXI-3) can be purified by a method knownin the field of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

(Method K)

Compound (XXI-1), Compound (XXI-2) and Compound (XXI-3) can be alsoproduced by the following method.

A compound (XXV)

    ZOCH.sub.2 CH.sub.2 NO.sub.2                               (XXV)

wherein Z is as defined above hereinafter referred to as Compound (XXV)!is condensed with a Compound (XX-1), (XX-2) or (XX-3) in the presence ofa base and subjected to protection of hydroxyl as necessary, to give acompound of the formula (XXVI) ##STR412## wherein R¹, Rr, Rs, Z and Zaare as defined above hereinafter referred to as Compound (XXVI-1),Compound (XXVI-2) or Compound (XXVI-3)!. The obtained compound iscondensed with formalin in the presence of a base and then subjected toprotection of hydroxyl as necessary to give a Compound (XXI-1), (XXI-2)or (XXI-3).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXVI-1), (XXVI-2) or (XXVI-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

Examples of the solvent to be used for the condensation with formalininclude water, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran,diethyl ether, ethylene glycol dimethyl ether, dimethylformamide,dimethyl sulfoxide, benzene, toluene, xylene, dioxane; methylenechloride, chloroform, dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXI-1), (XXI-2) or (XXI-3) can be purified by a method knownin the field of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

(Method L)

A compound of the formula (XXVII)

    WCH.sub.2 COOY                                             (XXVII)

wherein W is azide, nitro or amino protected by a suitable protectinggroup and Y is as defined above hereinafter referred to as Compound(XXVII)! is condensed, in the presence of a base, with a compound of theformula (XXVIII) ##STR413## wherein R¹, Rr, Rs and Hal are as definedabove hereinafter referred to as Compound (XXVIII-1), Compound(XXVIII-2) or Compound (XXVIII-3)! to give a compound of the formula(XXIX) ##STR414## wherein R¹, Rr, Rs, W and Y are as defined abovehereinafter referred to as Compound (XXIX-1), Compound (XXIX-2) orCompound (XXIX-3)!. The obtained compound is condensed with formalin inthe presence of a base and subjected to protection of hydroxyl asnecessary to give a compound of the formula (XXX) ##STR415## wherein R¹,Rr, Rs, W, Y and Z are as defined above hereinafter referred to asCompound (XXX-1), Compound (XXX-2) or Compound (XXX-3)!. The obtainedcompound is subjected to reduction of carboxyl with a suitable reducingagent and protection of hydroxyl as necessary to give a compound of theformula (XXXI) ##STR416## wherein R¹, Rr, Rs, W, Z¹ and Z² are asdefined above hereinafter referred to as Compound (XXXI-1), Compound(XXXI-2) or Compound (XXXI-3)! and the obtained compound is subjected toreduction of carbonyl with a suitable reducing agent, and reduction anddeprotection as necessary, to give a Compound (XXII-1), (I-22) or(I-23).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXIX-1), (XXIX-2) or (XXIX-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

Examples of the solvent to be used for the condensation with formalininclude water, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran,diethyl ether, ethylene glycol dimethyl ether, dimethylformamide,dimethyl sulfoxide, benzene, toluene, xylene, dioxane, methylenechloride, chloroform, dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes 2 days and thereaction period longer or shorter than the indicated period may be usedas necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXX-1), (XXX-2) or (XXX-3) can be purified by a method knownin the field of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the reducing agent to be used for the reduction of carboxylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used for the reduction of carboxylinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The reduction of carboxyl generally proceeds at a temperature of from-20° C. to 80° C. and a temperature lower or higher than thistemperature range may be selected on demand.

The reduction of carboxyl is generally carried out for 30 minutes to 10hours and the reaction period longer or shorter than the indicatedperiod may be used as necessary.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (XXXI-1),(XXXI-2) or (XXXI-3) can be purified by a method known in the field oforganic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the reducing agent to be used for the reduction of carbonylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used for the reduction of carbonylinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The reduction of carbonyl generally proceeds at a temperature of from-20° C. to 80° C. and a temperature lower or higher than thistemperature range may be selected on demand.

The reduction of carbonyl is generally carried out for 30 minutes to 10hours and the reaction period longer or shorter than the indicatedperiod may be used as necessary.

When (i) W=azide, examples of the reducing agent to be used for thereduction of azide include metallic reducing agent such as sodiumborohydride,.lithium borohydride or lithium aluminum hydride, andtransition metal such as palladium-carbon, platinum oxide, Raney nickel,rhodium or ruthenium for catalytic reduction.

Examples of the organic solvent to be used for the reduction of azideinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether, dioxane, acetone, ethyl acetate, acetic acid, benzene, toluene,xylene, dimethylformamide and dimethyl sulfoxide.

The reduction of azide generally proceeds at a temperature of from -20°C. to 80° C. and a temperature lower or higher than this temperaturerange may be selected on demand.

When (ii) W=nitro, examples of the reducing agent to be used for thereduction of nitro include metallic reducing reagent such as sodiumborohydride, lithium borohydride or lithium aluminum hydride, transitionmetal such as palladium-carbon, platinum oxide, Raney nickel, rhodium orruthenium for catalytic reduction, and metal such as iron, zinc or tin.

Examples of the solvent to be used for the reduction of nitro includewater, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether, dioxane, acetone, ethyl acetate, acetic acid, benzene, toluene,xylene, dimethylformamide and dimethyl sulfoxide.

The reduction of nitro generally proceeds at a temperature of from -20°C. to 80° C. and a temperature lower or higher than this temperaturerange may be selected on demand.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (XXII-1),(I-22) or (I-23) can be purified by a method known in the field oforganic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Accordingly, the instant method is applicable to the synthesis of thecompounds of the formulas (I-21) through (I-23).

(Method M)

Compound (XXX-1), Compound (XXX-2) and Compound (XXX-3) can be alsoproduced by the following method.

A compound (XXVIII) and a compound of the formula (XXXII) ##STR417##wherein W, Y and Z are as defined above hereinafter referred to asCompound (XXXII)! are condensed in the presence of a base to give aCompound (XXX-1), (XXX-2) or (XXX-3).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXX-1), (XXX-2) or (XXX-3) can be purified by a method knownin the field of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

(Method N)

When W=nitro, Compound (XXXI-1), (XXXI-2) and (XXXI-3) can be alsoproduced by the following method.

A compound (XXVIII-1), (XXVIII-2) or (XXVIII-3) and compound (XXXIII)

    CH.sub.3 NO.sub.2                                          (XXXIII)

hereinafter referred to as Compound (XXXIII)! are condensed in thepresence of a base to give a compound of the formula (XXXIV) ##STR418##wherein R¹, Rr and Rs are as defined above hereinafter referred to asCompound (XXXIV-1), Compound (XXXIV-2) or Compound (XXXIV-3)! and theobtained compound is condensed with formalin in the presence of a baseand subjected to protection of hydroxyl as necessary to give a Compound(XXXI-1), (XXXI-2) or (XXXI-3).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing-the protecting group on demand, theCompound (XXXIV-1), (XXXIV-2) or (XXXIV-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

Examples of the solvent to be used for the condensation with formalininclude water, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran,diethyl ether, ethylene glycol dimethyl ether, dimethylformamide,dimethyl sulfoxide, benzene, toluene, xylene, dioxane, methylenechloride, chloroform, dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXI-1), (XXXI-2) or (XXXI-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

(Method O)

Compound (XXXIV-1), Compound (XXXIV-2) and Compound (XXXIV-3) can bealso produced by the following method.

A Compound (XVII) and a compound of the formula (XXXV) ##STR419##wherein R¹, Rr, Rs and G are as defined above hereinafter referred to asCompound (XXXV-1), Compound (XXXV-2) or Compound (XXXV-3)! are condensedin the presence of a base to give a Compound (XXXIV-1), (XXXIV-2) or(XXXIV-3).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXIV-1), (XXXIV-2) or (XXXIV-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

(Method P)

When W=nitro, Compound (XXXI-1), Compound (XXXI-2) and Compound (XXXI-3)can be also produced by the following method.

A Compound (XXV) and a Compound (XXVIII-1), (XXVIII-2) or (XXVIII-3) arecondensed in the presence of a base to give a compound of the formula(XXXVI) ##STR420## wherein R¹, Rr, Rs and Z are as defined abovehereinafter referred to as Compound (XXXVI-1), Compound (XXXVI-2) orCompound (XXXVI-3)!. The obtained compound is condensed with formalin inthe presence of a base and subjected to protection of hydroxyl asnecessary to give a Compound (XXXI-1), (XXXI-2) or (XXXI-3).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXVI-1), (XXXVI-2) or (XXXVI-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

Examples of the solvent to be used for the condensation with formalininclude water, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran,diethyl ether, ethylene glycol dimethyl ether, dimethylformamide,dimethyl sulfoxide, benzene, toluene, xylene, dioxane, methylenechloride, chloroform, dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXI-1), (XXXI-2) or (XXXI-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

(Method Q)

Compound (X) can be also produced by the following method.

A Compound (II) and a Compound (XXVII) (W=nitro) are condensed in thepresence of a base to give a compound of the formula (XXXVII) ##STR421##wherein R¹ and Y are as defined above hereinafter referred to asCompound (XXXVII)!. The obtained compound is condensed with formalin inthe presence of a base and subjected to protection of hydroxyl asnecessary to give a compound of the formula (XXXVIII) ##STR422## whereinR¹, Y and Z are as defined above hereinafter referred to as Compound(XXXVIII)! and the obtained compound is subjected to reduction ofcarboxyl with a suitable reducing agent and protection of hydroxyl asnecessary to give a Compound (X).

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXVII) can be purified by a method known in the field oforganic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the solvent to be used for the condensation with formalininclude water, methanol, ethanol, tert-butyl alcohol, tetrahydrofuran,diethyl ether, ethylene glycol dimethyl ether, dimethylformamide,dimethyl sulfoxide, benzene, toluene, xylene, dioxane, methylenechloride, chloroform, dichloroethane and acetonitrile.

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, triethylamine, diisopropylethylamine and 1,8-diazabicyclo5.4.0!undeca-7-ene.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXVIII) can be purified by a method known in the field oforganic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the reducing agent to be used for the reduction of carboxylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used for the reduction of carboxylinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The reduction of carboxyl generally proceeds at a temperature of from-20° C. to 80° C. and a temperature lower or higher than thistemperature range may be selected on demand.

The reduction of carboxyl is generally carried out for 30 minutes to 10hours and the reaction period longer or shorter than the indicatedperiod may be used as necessary.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (X) canbe purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyor a method using an ion exchange resin.

(Method R)

A compound of the formula (XXXIX) ##STR423## wherein Q¹, Q², Z¹, Z², Gand α are as defined above hereinafter referred to as Compound (XXXIX-1)or Compound (XXXIX-2)! and a compound of the formula (XXXX) ##STR424##wherein Rv, Rw, X and β are as defined above hereinafter referred to asCompound (XXXX-1) or Compound (XXXX-2)! are condensed in the presence ofa base to give a compound of the formula (XXXXI) ##STR425## wherein Rv,Rw, X, Q¹, Q², Z¹, Z², α and β are as defined above hereinafter referredto as Compound (XXXXI-1) or Compound (XXXXI-2)! and the obtainedcompound is subjected to deprotection as necessary to give a compound(I-26) or (I-27).

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXXI-1) or (XXXXI-2) can be purified by a method known in thefield of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

In the instant method, a compound wherein X is sulfinyl or sulfonyl canbe obtained by oxidation of a compound wherein X is sulfur.

Accordingly, the instant method can be used for the synthesis of thecompounds of the formulas (I-26) and (I-27). It is also applicable tothe synthesis of the compounds (I-1), (I-2), (I-4), (I-5) and (I-7)through (I-11).

(Method S)

Compound (XXXXI-1) and Compound (XXXXI-2) can be also produced by thefollowing method.

A compound of the formula (XXXXII) ##STR426## wherein Q¹, Q², Z¹, Z², Xand α are as defined above hereinafter referred to as Compound(XXXXII-1) or Compound (XXXXII-2)! and a compound of the formula(XXXXIII) ##STR427## wherein Rv, Rw, G and β are as defined abovehereinafter referred to as Compound (XXXXIII-1) or Compound (XXXXIII-2)!are condensed in the presence of a base and the obtained compound issubjected to deprotection on demand to give a Compound (XXXXI-1) or(XXXXI-2).

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXXI-1) or (XXXXI-2) can be purified by a method known in thefield of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

(Method T)

Compound (XXXXI-1) and Compound (XXXXI-2) can be also produced by thefollowing method.

A compound of the formula (XXXXIV) ##STR428## wherein Rv, Rw, 6, X, αand β are as defined above hereinafter referred to as Compound(XXXXIV-1) or Compound (XXXXIV-2)! and a Compound (III) are condensed inthe presence of a base to give a compound of the formula (XXXXV)##STR429## wherein Rv, Rw, X, Q, Y, a and B are as defined abovehereinafter referred to as Compound (XXXXV-1) or Compound (XXXXV-2)!.The obtained compound is subjected to reduction with a suitable reducingagent and protection of hydroxyl and amino as necessary to give acompound (XXXXI-1) or (XXXXI-2).

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXXV-1) or (XXXXV-2) can be purified by a method known in thefield of organic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the reducing agent to be used for the reduction of carboxylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used for the reduction of carboxylinclude methanol, ethanol, tert-butyl. alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The reduction of carboxyl generally proceeds at a temperature of from-20° C. to 80° C. and a temperature lower or higher than thistemperature range may be selected on demand.

The reduction of carboxyl is generally carried out for 30 minutes to 10hours and the reaction period longer or shorter than the indicatedperiod may be used as necessary.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (XXXXI-1)or (XXXXI-2) can be purified by a method known in the field of organicsynthetic chemistry, such as solvent extraction, recrystallization,chromatography or a method using an ion exchange resin.

(Method U)

A Compound (XIV) is added with a compound of the formula (XXXXVI)##STR430## wherein R¹, Rr, Rs, M and n are as defined above hereinafterreferred to as Compound (XXXXVI-1), Compound (XXXXVI-2) or Compound(XXXXVI-3)! and the mixture is subjected to protection of hydroxyl asnecessary to give a compound of the formula (XXXXVII) ##STR431## whereinR¹, Rr, Rs, Q¹, Q², Z¹, Z² and Za are as defined above hereinafterreferred to as Compound (XXXXVII-1), Compound (XXXXVII-2) or Compound(XXXXVII-3)!. The obtained compound is subjected to deprotection ondemand to give a Compound (XXII-1), (I-22) or (I-23).

Examples of the solvent to be used for the addition includetetrahydrofuran, diethyl ether, ethylene glycol dimethyl ether,dimethylformamide, dimethyl sulfoxide, benzene, toluene, xylene,dioxane, methylene chloride, chloroform, dichloroethane andacetonitrile.

The addition generally proceeds at a temperature of from -100° C. to 80°C. and a temperature lower or higher than this temperature range may beselected on demand.

The addition is generally carried out for 30 minutes to 2 days and thereaction period longer or shorter than the indicated period may be usedas necessary.

After the addition is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound(XXXXVII-1), (XXXXVII-2) or (XXXXVII-3) can be purified by a methodknown in the field of organic synthetic chemistry, such as solventextraction, recrystallization, chromatography or a method using an ionexchange resin.

Accordingly, the instant method can be used for the synthesis of thecompounds of the formulas (I-21) through (I-23).

(Method V)

A compound of the formula (XXXXVIII) ##STR432## wherein Y is as definedabove hereinafter referred to as Compound (XXXXVIII)! and a Compound(II) are condensed in the presence of a base to give a Compound of theformula (XXXXIX) ##STR433## wherein R¹ and Y are as defined abovehereinafter referred to as Compound (XXXXIX)! and the obtained compoundis reacted with an amination agent of the formula (XXXXX)

    H.sub.2 N--Le                                              (XXXXX)

wherein Le means a leaving group such as 2,4-dinitrophenoxy, in thepresence of a base to give a compound of the formula (XXXXXI) ##STR434##wherein R¹ and Y are as defined above hereinafter referred to asCompound (XXXXXI)!. The obtained compound is subjected to reduction ofcarboxyl with a suitable reducing agent and deprotection as necessary togive a Compound (I-29).

Examples of the base to be used for the condensation include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the solvent to be used for the condensation include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The condensation generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The condensation is generally carried out for 30 minutes to 2 days andthe reaction period longer or shorter than the indicated period may beused as necessary.

After the condensation is carried out under the above-mentionedconditions or after removing the protecting group on demand, theCompound (XXXXIX) can be purified by a method known in the field oforganic synthetic chemistry, such as solvent extraction,recrystallization, chromatography or a method using an ion exchangeresin.

Examples of the base to be used for the amination include sodiumhydroxide, sodium methoxide, sodium ethoxide, sodium. hydride, potassiumhydride, lithium diisopropylamide, butyl lithium, lithiumhexamethyldisilazane, triethylamine, diisopropylethylamine and1,8-diazabicyclo 5.4.0!undeca-7-ene.

Examples of the solvent to be used for the amination include water,methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethyl ether,ethylene glycol dimethyl ether, dimethylformamide, dimethyl sulfoxide,benzene, toluene, xylene, dioxane, methylene chloride, chloroform,dichloroethane and acetonitrile.

The amination generally proceeds at a temperature of from -20° C. to150° C. and a temperature lower or higher than this temperature rangemay be selected on demand.

The amination is generally carried out for 30 minutes to 2 days and thereaction period longer or shorter than the indicated period may be usedas necessary.

After the amination is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (XXXXXI)can be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyor a method using an ion exchange resin.

Examples of the reducing agent to be used for the reduction of carboxylinclude metallic reducing reagent such as sodium borohydride, lithiumborohydride or lithium aluminum hydride, and diborane.

Examples of the organic solvent to be used for the reduction of carboxylinclude methanol, ethanol, tert-butyl alcohol, tetrahydrofuran, diethylether and ethylene glycol dimethyl ether.

The reduction of carboxyl generally proceeds at a temperature of from-20° C. to 80° C. and a temperature lower or higher than thistemperature range may be selected on demand.

The reduction of carboxyl is generally carried out for 30 minutes to 10hours and the reaction period longer or shorter than the indicatedperiod may be used as necessary.

After the reduction is carried out under the above-mentioned conditionsor after removing the protecting group on demand, the Compound (I-29)can be purified by a method known in the field of organic syntheticchemistry, such as solvent extraction, recrystallization, chromatographyor a method using an ion exchange resin.

The instant method can be used for the synthesis of the compounds of theformulas (I-1) through (I-18), preferably for the synthesis of thecompounds of the formulas (I-12) and (I-13).

(Method W)

Of the compounds of the formula (I) of the present invention, a compoundwherein R is --CH(OH)Rr when it is a compound of the formula ##STR435##wherein Rr is as defined above hereinafter referred to as Compound(XXXXXII)! or a derivative at carboxyl group thereof or a compound(XXXXXII) wherein the α-position of alkyl at Rr, which may have a doublebond or carbonyl in the chain, is substituted by hydroxyl, can beproduced by reduction, hydrogenation, ozonolysis or oxidation known perse, which may be used solely or in combination, of a correspondinglactone compound or a compound wherein amino or hydroxy of a Compound(XXXXXII) or lactone compound is protected by a protecting group.

Examples of the derivative at the carboxyl group of the Compound(XXXXXII) include ester (e.g. methyl ester, ethyl ester, benzyl ester,p-nitrobenzyl ester, trimethylsilyl ester, tert-butyldimethylsilylester), acid halide (e.g. acid chloride), acid anhydride and mixed acidanhydride.

A Compound (I) wherein Rr is an α-position hydroxyl-substituted alkyl ispreferably produced by using the aforementioned lactone compound as astarting material.

Reduction proceeds in a solvent inert to the reaction and in thepresence of a metal hydride complex at a temperature from under coolingto under refluxing. Examples of the metal hydride complex includealuminum hydride, lithium aluminum hydride, lithium aluminumhydride-aluminum chloride, lithium trimethoxy aluminum hydride, sodiumbis(2-methoxyethoxy)aluminum hydride, diisobutyl aluminum hydride,sodium borohydride, sodium hydride, lithium borohydride and borohydride,and examples of the solvent include alcohol solvents such as methanol,ethanol, isopropanol and diethylene glycol, hydrocarbon solvents such asbenzene, toluene and xylene, halohydrocarbon solvents such as methylenechloride, dichloroethane and chloroform, ether solvents such as diethylether, dipropyl ether, tetrahydrofuran and dioxane, dimethylformamide,and dimethyl sulfoxide, which may be used solely or in combination.

The reduction may be catalytic reduction using zinc-hydrochloric acidsaturated acetic anhydride, copper-chromite catalyst, palladium-carbon,Raney nickel or rhenium oxide, or electroreduction. These reactionsproceed in a manner similar to the reaction known per se.

The hydrogenation generally proceeds according to a method known per seusing a conventional catalyst such as a palladium, nickel or platinumcatalyst. In the reaction, a solvent inert to the reaction may be usedand examples thereof are as mentioned above.

In the present invention, the compound obtained by the above-mentionedreactions can be used as a starting material.

Of the Compounds (XXXXXII), a compound wherein Rr is an α-positionhydroxyl-substituted alkyl which may have a double bond or carbonyl inthe chain and lactone compound thereof are known compounds reported inJapanese Patent Unexamined Publication Nos. 104087/1989 and 128347/1991mentioned above and are produced according to the method describedtherein. Of the Compounds (XXXXXII), a compound wherein Rr is an alkylwhich may have a double bond or carbonyl in the chain, such asheptadecyl, is produced, for example, by fermentation or by using acompound (XXXXXIII) produced by the fermentation and having the formula##STR436## as a starting material. Examples of the microorganism capableof producing the compound (XXXXXIII) include those belonging toAscomycetes or Fungi Imperfecti, particularly the genera Isaria andMycelia belonging to the Fungi Imperfecti and the genus Myriococcum (thegenus Thielavia) belonging to Ascomycetes, which are respectivelydeposited at American Type Culture Collection as Isaria sinclairii ATCCNo. 24400, Myriococcum albomyces ATCC No. 16425 and Mycelia steriliaATCC No. 20349. Also, Myriococcum albomyces ATCC No. 16425 has beendeposited at the Institute of Fermentation, Osaka as IF032292.

Compound (XXXXXIII) can be produced, for example, by a mutant strainobtained by mutating the above-mentioned strain by a conventionalartificial mutating method using ultraviolet rays, high frequencyradiation, drug or the like.

The Compound (XXXXXIII)-producing cell may be cultured in variousculture media containing conventional nutrition sources for mold. Forexample, a medium may contain glucose, starch, glycerin, sugar syrup,dextrin, molasses, maltose, xylose or the like as a carbon source and aninorganic or organic nitrogen compound such as corn steep liquor,peptone, yeast extract, potato brew, meat broth, soybean powder, wheatgerm, potassium nitrate, sodium nitrate, ammonium sulfate, casein,gluten meal, cottonseed powder or feather powder as a nitrogen source.Besides these, there may be contained additives conventionally used forculture such as conventional inorganic salt, organic or inorganicsubstance which promotes the growth of cell and enhances production ofthe Compound (XXXXXIII), and antifoaming agent.

While the culture method is subject to no particular limitation, aerobicsubmerged culture is desirable. The temperature appropriate for theculture is 20°-35° C., preferably 25°-30° C. for the microorganismsbelonging to the genus Isaria and 30°-50° C., preferably 35°-45° C. forthe microorganisms belonging to the genus Myriococcum or Mycelia.

The Compound (XXXXXIII) produced in the culture medium is isolatedtherefrom by conventional steps such as extraction and adsorption whichmay be used in combination as necessary. For example, in the case of amicroorganism belonging to the genus Isaria such as Isaria sinclairii,the Compound (XXXXXIII) is taken out from the culture by filtering offthe insoluble matters such as cells from the culture, isolation bycentrifugation, passing the culture filtrate through Amberlite XAD-2(trade mark) and adsorbing Compound (XXXXXlII). The Compound (XXXXXIII)thus obtained is eluted with, for example, methanol and the eluate isfractionated by reversed phase chromatography, whereby a highly purifiedproduct of Compound (XXXXXlII) can be obtained. In the case of amicroorganism belonging to the genus Myriococcum or the genus Mycelia,such as Myriococcum albomyces, Mycelia sterilia or the like, cells areseparated from the culture by filtration, centrifugation and the likeand the culture filtrate is treated in the same manner as in the case ofthe microorganisms belonging to the genus Isaria. The Compound(XXXXXIII) is extracted from the separated cells by the use of methanoland the extract is treated with Amberlite XAD-2 in the same manner aswith the filtrate above and purified by chromatography andrecrystallization.

The 2-amino-1,3-propanediol compounds, isomers thereof and salts thereofof the present invention show superior immunosuppressive effect and areuseful as a suppressant of rejection in organ or bone marrowtransplantation in mammals inclusive of human, cow, horse, dog, mouse,rat etc., an agent for the prevention and treatment of autoimmunediseases such as rheumatoid arthritis, atopic eczema (atopicdermatitis), Behcet's disease, uvea diseases, systemic lupuserythematosus, Sjogren's syndrome, polysclerosis, myasthenia gravis,diabetes type I, endocrine eye disorders, primary biliary cirrhosis,Crohn's disease, glomerulonephritis, sarcoidosis, psoriasis, pemphigus,aplastic anemia, idiopathic thrombocytopenic purpura, allergy,polyarteritis nodosa, progressive systemic sclerosis, mixedconnective-tissue disease, aortitis syndrome, polymyositis,dermatomyositis, Wegener's granulomatosis, ulcerative colitis, activechronic hepatitis, autoimmune hemolytic anemia, Evans syndrome,bronchial asthma, pollinosis and so on, and a reagent for use inmedicine and pharmacy. Also, the compounds protected with a protectinggroup are useful as intermediates for the synthesis of the compoundshaving superior pharmacological actions as recited above.

When these compounds are used as pharmaceuticals, an effective amountthereof is generally admixed with carrier, excipient, diluent and so onand formulated into powder, capsule, tablet, injection or the like forthe administration to patients. A lyophilized preparation may beproduced by a method known per se.

While the dose of these compounds varies depending on disease, symptom,body weight, sex, age and so on, they are administered, for example, toan adult daily by 0.01-10 mg (potency) in a single to several timesdivided doses when suppressing rejection in kidney transplantation.

Moreover, the compounds of the present invention can be used incombination with other immunosuppressant such as cyclosporin,azathioprine, steroids or FK-506 (EP-A184162).

The present invention is hereinafter explained in detail by illustratingexamples, to which the present invention is not limited.

EXAMPLE 1

(1) Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dryethanol and 1.13 g of sodium ethoxide was added thereto. A solution of4.7 g of tetradecyl bromide in 20 ml of ethanol was added to the mixedsolution while stirring at room temperature. The inside of the reactionvessel was displaced with nitrogen and the mixture was refluxed forabout 15 hours. Then, the mixture was neutralized with a 1N aqueoushydrochloric acid solution and concentrated. The concentrate waspurified by silica gel column chromatography to give 3.5 g of diethyl2-acetamido-2-tetradecylmalonate.

melting point=58.5°-60.5° C.

IR(KBr): 3280, 2970, 2930, 2860, 1750, 1655, 1525, 1480, 1220, 1030 cm⁻¹

(2) Diethyl 2-acetamido-2-tetradecylmalonate (3.40 g) was dissolved in200 ml of dry tetrahydrofuran. The reaction vessel was equipped with acalcium chloride tube and 1.58 g of lithium aluminum hydride was addedthereto in an ice water bath, followed by stirring. After stirring themixture at room temperature for 30 minutes, 3.0 ml of water was addedthereto to stop the reaction. The reaction mixture was concentratedunder reduced pressure and 100 ml of acetic anhydride and 80 ml ofpyridine were added to the concentrate. The mixture was stirred at roomtemperature overnight. The reaction mixture was poured into ice water tomake the total amount 1606 ml and extracted three times with 500 ml ofethyl acetate. The ethyl acetate layers were combined and washed with a1N aqueous hydrochloric acid solution, a saturated aqueous sodiumhydrogencarbonate solution and a saturated aqueous sodium chloridesolution in order. The mixture was dried over anhydrous magnesiumsulfate and concentrated. The concentrate was purified by silica gelcolumn chromatography to give 1.35 g of2-acetamido-1,3-diacetoxy-2-tetradecylpropane.

melting point=84.0°-85.5° C.

IR(KBr): 3310, 2950, 2920, 2840, 1750, 1655, 1550, 1470, 1375, 1255,1230, 1035, 900 cm⁻¹

EXAMPLE 2

2-Acetamido-1,3-diacetoxy-2-tetradecylpropane (1.25 g) was dissolved in100 ml of methanol and 19.4 ml of a 1N aqueous sodium hydroxide solutionwas added thereto. The mixture was refluxed under heating for 6 hours.The mixture was neutralized with a 1N aqueous hydrochloric acid solutionand concentrated under reduced pressure. The concentrate was washed withwater and ethyl acetate:hexane=1:1 in order to give 791 mg of2-amino-2-tetradecyl-1,3-propanediol hydrochloride.

melting point=96.5°-98.5° C.

Rf: 0.55 (chloroform:methanol:water=65:35:5)

IR(KBr): 3520, 3450, 3300, 3050, 2920, 2850, 1630, 1530, 1470, 1290,1070, 1050 cm⁻¹

EXAMPLE 3

(1) Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dryethanol and 1.13 g of sodium ethoxide was added thereto. A solution of5.5 g of hexadecyl bromide in 20 ml of ethanol was added thereto at roomtemperature with stirring. The inside of the reaction vessel wasdisplaced with nitrogen and the mixture was refluxed for about 15 hours.The mixture was neutralized with a 1N aqueous hydrochloric acid solutionand concentrated. The concentrate was purified by silica gel columnchromatography to give 4.37 g of diethyl2-acetamido-2-hexadecylmalonate.

melting point=65.0°-67.0° C.

IR(KBr): 3300, 2920, 2850, 1745, 1650, 1515, 1210, 1020 cm⁻¹

(2) Diethyl 2-acetamido-2-hexadecylmalonate (4.30 g) was dissolved in200 ml of dry tetrahydrofuran and the reaction vessel was equipped witha calcium chloride tube. Thereto was added 1.90 g of lithium aluminumhydride in an ice water bath and the mixture was stirred. After stirringthe mixture at room temperature for 30 minutes, 3.6 ml of water wasadded thereto to stop the reaction. The reaction mixture wasconcentrated under reduced pressure and 100 ml of acetic anhydride and80 ml of pyridine were added to the residue. The mixture was stirred atroom temperature overnight. The reaction mixture was poured into icewater to make the total amount 1600 ml and extracted three times with500 ml of ethyl acetate. The ethyl acetate layers were combined andwashed with a 1N aqueous hydrochloric acid solution, a saturated aqueoussodium hydrogencarbonate solution and a saturated aqueous sodiumchloride solution in order. The resultant mixture was dried overanhydrous magnesium sulfate and concentrated. The concentrate waspurified by silica gel column chromatography to give 1.83 g of2-acetamido-1,3-diacetoxy-2-hexadecylpropane.

melting point=84°-86° C.

IR(KBr): 3300, 2920, 2850, 1740, 1655, 1560, 1390, 1270, 1240, 1055 cm⁻¹

EXAMPLE 4

2-Acetamido-1,3-diacetoxy-2-hexadecylpropane (1.75 g) was dissolved in100 ml of methanol and 23.8 ml of a 1N aqueous sodium hydroxide solutionwas added thereto. The mixture was refluxed under heating for 6 hours.The mixture was neutralized with a 1N aqueous hydrochloric acid solutionand concentrated under reduced pressure. The concentrate was washed withwater and ethyl acetate:hexane=1:1 in order to give 892 mg of2-amino-2-hexadecyl-1,3-propanediol hydrochloride.

melting point=100.5°-104.0° C.

Rf: 0.55 (chloroform:methanol:water=65:35:5)

IR(KBr): 3350, 2920, 2850, 1590, 1470, 1050 cm⁻¹

EXAMPLE 5

(1) Diethyl 2-acetamidomalonate (5.0 g) was dissolved in 64 ml of dryethanol and 1.71 g of sodium ethoxide was added thereto. A solution of8.4 g of octadecyl bromide in 20 ml of dry ethanol was added theretowhile stirring at room temperature. The inside of the reaction vesselwas displaced with nitrogen and the mixture was refluxed for about 15hours. The mixture was neutralized with a 1N aqueous hydrochloric acidsolution and concentrated. The concentrate was purified by silica gelcolumn chromatography to give 6.4 g of diethyl2-acetamido-2-octadecylmalonate.

melting point=70°-71° C.

¹ H-NMR (200 MHz, CDCl₃) δ: 6.77 (1H, br.s, --NH--) 4.24 (4H, q, J=7.16Hz, --OCH₂ ×2), 2.35-2.26 (2H, m, C₃ --Ha, Hb), 2.03 (3H, s, CH₃CONH--), 1.25 (38H, m, O--CH₂ --CH₃ ×2, CH₂ ×16), 0.88 (3H, t, J=6.47Hz, CH₃)

IR: 3260, 2910, 2850, 1745, 1640, 1515, 1210, 1020 cm⁻¹

(2) Diethyl 2-acetamido-2-octadecylmalonate (3.0 g) was dissolved in drytetrahydrofuran and the reaction vessel was equipped with a calciumchloride tube. In an ice water bath, 1.2 g of lithium aluminum hydridewas added thereto and the mixture was stirred. Then, the mixture wasstirred at room temperature for 30 minutes and 2.31 g of water was addedthereto to stop the reaction. The reaction mixture was concentratedunder reduced pressure and 130 ml of acetic anhydride and 120 ml ofpyridine were added to the concentrate. The mixture was stirred at roomtemperature overnight. The resultant mixture was poured into ice waterto make the total amount 2200 ml and extracted three times with 700 mlof ethyl acetate. The ethyl acetate layers were combined and washed witha 1N aqueous hydrochloric acid solution, an aqueous sodiumhydrogencarbonate solution and an aqueous sodium chloride solution inorder. The mixture was dried over anhydrous magnesium sulfate andconcentrated. The concentrate was purified by silica gel columnchromatography to give 1.7 g of2-acetamido-1,3-diacetoxy-2-octadecylpropane.

melting point=90°-91° C.

¹ H-NMR (200 MHz, CDCl₃) δ: 5.64 (1H, br.s, --NH--), 4.30 (4H, s, --CH₂O--×2), 2.09 (6H, s, OCOCH₃ ×2), 1.97 (3H, s, NHCOCH₃ ), 1.25 (34H,br.s, CH₂ ×17), 0.88 (3H, t, J=6.47 Hz, CH₃)

IR: 3280, 2920, 2850, 1750, 1735, 1645, 1565, 1385, 1270, 1240, 1045cm⁻¹

EXAMPLE 6

2-Acetamido-1,3-diacetoxy-2-octadecylpropane (1.00 g) was dissolved in26 ml of methanol and 6.4 ml of a 1N aqueous sodium hydroxide solutionwas added thereto. The mixture was refluxed under heating for 6 hours.The mixture was neutralized with a 1N aqueous hydrochloric acid solutionand concentrated under reduced pressure. The concentrate was washed withwater and ethyl acetate:hexane=1:1 in order to give 639 mg of2-amino-2-octadecyl-1,3-propanediol hydrochloride.

melting point=108.5°-109.5° C.

¹ H-NMR (200 MHz, CD₃ OD) δ: 3.64 (2H, d, J=11.48 Hz, --CH₂ --O--), 3.57(2H, d, J=11.47 Hz, --CHb--O--), 1.28 (34H, br.s, CH₂ ×17), 0.90 (3H, t,J=6.35 Hz, --CH₃)

IR: 3275, 2900, 2840, 1630, 1600, 1530, 1465, 1290, 1050 cm⁻¹

EXAMPLE 7

2-Amino-2-octadecyl-1,3-propanediol hydrochloride (100 mg) as obtainedin Example 6 was dissolved in 200 ml of methanol and the mixture wasdropwise added to 50 ml of Diaion WA-10 (trade mark, anion exchangeresin). The solvent of the eluate was distilled away to give 64 mg of2-amino-2-octadecyl-1,3-propanediol.

melting point=76.0°-80.0° C.

IR: 3290, 3175, 2910, 2850, 1590, 1580, 1480, 1065, 1050, 1000 cm⁻¹

EXAMPLE 8

(1) Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dryethanol and 1.3 g of sodium ethoxide was added thereto. A solution of6.5 g of docosyl bromide in 20 ml of dry ethanol was added thereto whilestirring at room temperature. The inside of the reaction vessel wasdisplaced with nitrogen and the mixture was refluxed for about 15 hours.The mixture was neutralized with a 1N aqueous hydrochloric acid solutionand concentrated. The concentrate was purified by silica gel columnchromatography to give 4.2 g of diethyl 2-acetamido-2-docosylmalonate.

melting point=79°-80° C.

IR(KBr): 3300, 2925, 2860, 1750, 1655, 1520, 1220 cm⁻¹

(2) Diethyl 2-acetamido-2-docosylmalonate (4.15 g) was dissolved in drytetrahydrofuran and the reaction vessel was equipped with a calciumchloride tube. In an ice water bath, 1.4 g of lithium aluminum hydridewas added thereto and the mixture was stirred. The mixture was stirredat room temperature for 30 minutes and 2.31 g of water was added theretoto stop the reaction. The reaction mixture was concentrated underreduced pressure and 130 ml of acetic anhydride and 120 ml of pyridinewere added thereto. The mixture was stirred at room temperatureovernight. The reaction mixture was poured into ice water to make thetotal amount 2200 ml and extracted three times with 700 ml of ethylacetate. The ethyl acetate layers were combined and washed with a 1Naqueous hydrochloric acid solution, a saturated aqueous sodiumhydrogencarbonate solution and a saturated aqueous sodium chloridesolution in order. The mixture was dried over anhydrous magnesiumsulfate and concentrated. The concentrate was purified by silica gelcolumn chromatography to give 1.8 g of2-acetamido-1,3-diacetoxy-2-docosylpropane.

melting point=94°-95° C.

IR(KBr): 3280, 2920, 2850, 1750, 1655, 1520, 1480, 1220 cm⁻¹

EXAMPLE 9

2-Acetamido-1,3-diacetoxy-2-docosylpropane (1.5 g) was dissolved in 40ml of methanol and 9.6 ml of a 1N aqueous sodium hydroxide solution wasadded thereto. The mixture was refluxed under heating for 6 hours. Themixture was neutralized with a 1N aqueous hydrochloric acid solution andconcentrated under reduced pressure. The concentrate was washed withwater and ethyl acetate:hexane=1:1 in order to give 846 mg of2-amino-2-docosyl-1,3-propanediol hydrochloride.

melting point=109.0°-110.5° C.

Rf: 0.55 (chloroform:methanol:water=65:35:5)

IR(KBr): 3500, 3450, 3290, 2920, 2850, 1640, 1530, 1470, 1060 cm⁻¹

EXAMPLE 10

(1) Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dryethanol and 1.3 g of sodium ethoxide was added thereto. A solution of6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto whilestirring at room temperature. The inside of the reaction vessel wasdisplaced with nitrogen and the mixture was refluxed for about 15 hours.The mixture was neutralized with a 1N aqueous hydrochloric acid solutionand concentrated. The concentrate was purified by silica gel columnchromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate.

melting point=76.5°-77.5° C.

IR(KBr): 2920, 2850, 1750, 1655, 1520, 1480, 1220 cm⁻¹

(2) Diethyl 2-acetamido-2-icosylmalonate (3.7 g) was dissolved in drytetrahydrofuran. The reaction vessel was equipped with a calciumchloride tube and the mixture was cooled to 0° C. Lithium aluminumhydride (1.4 g) was added thereto and the mixture was stirred. Themixture was stirred at room temperature for 30 minutes and 2.31 g ofwater was added thereto to stop the reaction. The reaction mixture wasconcentrated under reduced pressure and 130 ml of acetic anhydride and120 ml of pyridine were added thereto. The mixture was stirred at roomtemperature overnight. The reaction mixture was poured into ice water tomake the total amount 2200 ml and extracted three times with 700 ml ofethyl acetate. The ethyl acetate layers were combined and washed with a1N aqueous hydrochloric acid solution, a saturated aqueous sodiumhydrogencarbonate solution and a saturated aqueous sodium chloridesolution in order. The mixture was dried over anhydrous magnesiumsulfate and concentrated. The concentrate was purified by silica gelcolumn chromatography to give 1.7 g of2-acetamido-1,3-diacetoxy-2-icosylpropane.

melting point=93°-94° C.

IR(KBr): 3280, 2920, 2855, 1775, 1755, 1650, 1565, 1480, 1385, 1270,1245, 1045 cm⁻¹

EXAMPLE 11

2-Acetamido-1,3-diacetoxy-2-icosylpropane (1.5 g) was dissolved in 40 mlof methanol and 9.6 ml of a 1N aqueous sodium hydroxide solution wasadded thereto. The mixture was refluxed under heating for 6 hours. Themixture was neutralized with a 1N aqueous hydrochloric acid solution andthe reaction mixture was concentrated under reduced pressure. Theconcentrate was washed with water and ethyl acetate:hexane=1:1 in orderto give 817 mg of 2-amino-2-icosyl-1,3-propanediol hydrochloride.

melting point=109.5°-111.0° C.

Rf: 0.55 (chloroform:methanol:water=65:35:5)

IR(KBr): 3300, 2910, 2850, 1640, 1600, 1480, 1065, 1050 cm⁻¹

EXAMPLE 12

(1) Diethyl 2-acetamidomalonate (15 g) was dissolved in 200 ml of dryethanol and 5.6 g of sodium ethoxide was added thereto. To the reactionmixture, 22 g of 9-octadecenyl chloride was added while stirring at roomtemperature. The inside of the reaction vessel was displaced withnitrogen and the mixture was refluxed for about 15 hours. The mixturewas neutralized with ethanol-concentrated hydrochloric acid (11:1) andconcentrated. The concentrate was purified by silica gel columnchromatography to give 1.3 g of diethyl2-acetamido-2-(9-octadecenyl)malonate as a colorless, oily and viscoussubstance.

¹ H-NMR (200 MHz, CDCl₃) δ: 6.765 (1H, br.s, --NH--), 5.340-5,310 (2H,m, CH═CH), 4.240 (4H, q, J=7.4 Hz, --OCH₂ --×2), 2.032 (3H, s, CH₃ CON),1.990 (4H, m, CH₂ CH═×2), 1.252 (26H, m, CH₂ ×13), 1.252 (6H, t, J=7.2Hz, OCH₂ --CH₃ ×2), 0.880 (3H, t, J=6.5 Hz, CH₃)

(2) Diethyl 2-acetamido-2-(9-octadecenyl)malonate (1.3 g) was dissolvedin 30 ml of dry tetrahydrofuran and 450 mg of lithium aluminum hydridewas added thereto under ice-cooling. The inside of the reaction vesselwas displaced with dry nitrogen and the mixture was stirred. Then, themixture was stirred at room temperature for 2 hours and 1 ml of waterwas added thereto to stop the reaction. The reaction mixture wasconcentrated under reduced pressure and 10 ml of acetic anhydride and 5ml of pyridine were added thereto. The mixture was stirred at roomtemperature overnight. Water was added to the reaction mixture underice-cooling to make the total amount about 100 ml and the mixture wasextracted twice with 50 ml of ethyl acetate. The ethyl acetate layerswere combined and washed with a 1N aqueous hydrochloric acid solution, asaturated aqueous sodium hydrogencarbonate solution and a saturatedaqueous sodium chloride solution in order. The mixture was dried overanhydrous magnesium sulfate and concentrated to give 430 mg of2-acetamido-1,3-diacetoxy-2-(9-octadecenyl)propane as a colorless, oilyand viscous substance.

IR(CHCl₃): 3460, 3420, 3010, 2940, 2860, 1750, 1690, 1520, 1475, 1390,1380, 1240(br), 1045, 990 cm⁻¹

EXAMPLE 13

2-Acetamido-1,3-diacetoxy-2-(9-octadecenyl)propane (332 mg) wasdissolved in 30 ml of methanol and 7.8 ml of a 1N aqueous sodiumhydroxide solution was added thereto. The mixture was refluxed underheating overnight. The mixture was neutralized withmethanol-concentrated hydrochloric acid (11:1) and concentrated underreduced pressure. The concentrate was dissolved in methanol-water (1:1)and subjected to reversed phase column chromatography packing:Sep-Pak(C₁₈)!. After washing, the mixture was eluted with methanol. Theeluate was concentrated to give 209 mg of2-amino-2-(9-octadecenyl)-1,3-propanediol hydrochloride as a colorless,oily and viscous substance.

¹ H-NMR (200 MHz, CD₃ OD) δ: 5.385-5.315 (2H, m, CH═CH), 3.616 (2H, d,J=11.4 Hz, OCH_(2a) ×2), 3.548 (2H, d, J=11.4 Hz, OCH_(2b) ×2),2.071-1.957 (4H, m, CH₂ CH═×2), 1.665-1.580 (2H, m, CCH₂), 1.39-1.28(24H, m, CH₂ ×12), 0.896 (3H, t, J=6 Hz, CH₃)

IR: 3300(br), 2920, 2850, 1600, 1500, 1465, 1050, 965 cm⁻¹

EXAMPLE 14

(1) Sodium (0.23 g) was added to 15 ml of absolute ethanol and themixture was stirred at room temperature for 30 minutes in a nitrogenflow to give a 10 mmol solution of sodium ethoxide in ethanol. To thissolution, 1.98 g of diethyl 2-acetamidomalonate was added and themixture was heated at 50° C. for 30 minutes in a stream of nitrogen.3-Phenylpropyl bromide was added thereto at room temperature and themixture was refluxed under heating for 24 hours. The mixture wasneutralized with dilute hydrochloric acid and ethanol was distilledaway. The resultant residue was extracted with ethyl acetate. The ethylacetate layer was washed with water and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue was purified bysilica gel column chromatography (ethyl acetate:hexane=1:4-1:1) andrecrystallized from diisopropyl ether-hexane to give 800 mg of diethyl2-acetamido-2-(3-phenylpropyl)malonate as white crystals.

melting point=76°-77° C.

Rf: 0.58 (ethyl acetate:hexane=1:1)

¹ H-NMR (90 MHz, CDCl₃) δ: 1.22 (3H, t, J=7 Hz), 1.10-1.56 (4H, m), 2.02(3H, s), 2.28-2.75 (2H, m), 4.21 (4H, q, J=7 Hz), 6.75 (1H, br.s),7.02-7.42 (5H, m)

IR ν: 3259, 2980, 2863, 1738, 1648 cm⁻¹

MS(EI): 335(M⁺)

(2) A solution (50 ml) of 1.0 g of the above-mentioned compound and 136mg of lithium borohydride in tetrahydrofuran was refluxed under heatingfor 1 hour in a nitrogen flow. The reaction mixture was poured into 100ml of ice water and extracted with ethyl acetate. The extract was washedand dried, and the solvent was distilled away. The residue was purifiedby silica gel column chromatography (methanol:chloroform=1:20) to give720 mg of 2-acetamido-2-(3-phenylpropyl)-1,3-propanediol as a colorless,oily substance.

Rf: 0.30 (ethyl acetate)

¹ H-NMR (90 MHz, CDCl₃) δ: 1.47-1.89 (4H, m), 2.00 (3H, s), 2.44-2.84(2H, m), 3.73 (4H, dd, J=7 Hz, 15 Hz), 3.37-4.17 (2H, m), 5.51-5.97 (1H,m), 7.00-7.45 (5H, m)

IRν: 3294, 2938, 1652 cm⁻¹

MS(EI): 251(M⁺)

EXAMPLE 15

2-Acetamido-2-(3-phenylpropyl)-1,3-propanediol (600 mg) was dissolved in25 ml of methanol and 11.9 ml of a 1N aqueous sodium hydroxide solutionwas added thereto. The mixture was refluxed under heating for 6 hours.The mixture was poured into 30 ml of ice water and neutralized withdilute hydrochloric acid. The solvent was distilled away. Chloroform wasadded to the residue for extraction and the chloroform layer was washedand dried. The solvent was distilled away and the residue was purifiedby column chromatography (chloroform:methanol=9:1-4:1) to give 250 mg of2-amino-2-(3-phenylpropyl)-1,3-propanediol as a pale yellow, oilysubstance.

Rf: 0.22 (methanol:chloroform=1:4)

¹ H-NMR (90 MHz, CDCl₃) δ: 1.11-1.98 (4H, m), 2.43-2.75 (2H, m),3.15-4.03 (4H, 3.62 (4H, br.s), 7.19 (5H, s)

IR ν: 3347, 3023, 2937, 1583 cm⁻¹

MS(EI): 209(M⁺)

EXAMPLE 16

(1) A solution of 5.42 g of cinnamyl bromide, 5.43 g of diethyl2-acetamidomalonate and 1.87 g of sodium ethoxide in 70 ml of ethanolwas refluxed under heating for 2 hours under a nitrogen atmosphere. Themixture was poured into 200 ml or ice water and extracted with ethylacetate. The extract was dried over anhydrous sodium sulfate and thesolvent was distilled away. The residue was purified by silica gelchromatography (ethyl acetate:hexane=1:10-1:3) to give 2.68 g of diethyl2-acetamido-2-(3-phenyl-2-propenyl)malonate as white crystals.

melting point=70°-75° C.

Rf: 0.38 (ethyl acetate:hexane=1:5)

¹ H-NMR (CDCl₃ /TMS) δ: 1.31 (6H, t, J=7.5 Hz), 1.56 (2H, s), 2.09 (3H,s), 4.28 (4H, q, J=7.5 Hz), 6.30-6.80 (2H, m), 7.27 (5H, s)

IR(KBr): 3280, 2990, 1740, 1640 cm⁻¹

(2) A solution (80 ml) of 2.50 g of the above-mentioned compound and1.63 g of lithium borohydride in tetrahydrofuran was refluxed underheating for 2 hours under a nitrogen atmosphere. After the reaction, thesolvent was distilled away and the residue was evaporated to dryness.Acetic anhydride (14 ml) and 50 ml of pyridine were added to the residueand the mixture was stirred at room temperature overnight. The mixturewas poured into ice water and extracted with ethyl acetate. The extractwas washed with 2N hydrochloric acid, a saturated aqueous sodiumbicarbonate solution and saturated brine in order and dried. The solventwas distilled away and the residue was purified by silica gel columnchromatography (ethyl acetate:hexane=3:1) to give 200 mg of2-acetamido-1,3-diacetoxy-2-(3-phenyl-2-propenyl)propane as whitecrystals.

melting point=88°-90° C.

Rf: 0.70 (ethyl acetate)

¹ H-NMR (CDCl₃ /TMS) δ: 1.96 (3H, s), 2.07 (6H, s), 2.82 (2H, d, J=7.5Hz), 4.36 (4H, s)

IR(KBr): 3311, 3084, 1750, 1655, 1560 cm⁻¹

MS(EI): 333(M⁺)

elemental analysis: calculated C 64.85, H 6.95, N 4.20 found C 64.85, H6.88, N 4.15

EXAMPLE 17

2-Acetamido-1,3-diacetoxy-2-(3-phenyl-2-propenyl)propane (170 mg) wasdissolved in 6 ml of methanol and 6 ml of a 1N aqueous sodium hydroxidesolution was added thereto. The mixture was refluxed under heating for 3hours. After the reaction, the solvent was distilled away and theresidue was purified by silica gel column chromatography(methanol:chloroform=1:30-1:6) to give 70 mg of2-amino-2-(3-phenyl-2-propenyl)-1,3-propanediol as pale brown crystals.

Rf: 0.14 (methanol:chloroform=1:10)

IR(KBr): 3367, 2935, 1556 cm⁻¹

EXAMPLE 18

(1) 1-Phenyl-1-propyn-3-ol (5 g), 5.1 g of tosyl chloride and 20 ml ofpyridine were stirred at room temperature for 1 hour. The reactionmixture was poured into 100 ml of ice water and extracted with ethylacetate. The oil layer was washed with 1N hydrochloric acid andsaturated brine and dried over anhydrous sodium sulfate. The solvent wasdistilled away. The residue was purified by silica gel columnchromatography (ethyl acetate:hexane=1:5) to give 2.54 g of3-phenyl-2-propynyl chloride as a pale yellow, oily substance.

Rf: 0.81 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 4.37 (2H, s), 7.23-7.60 (5H, m)

IR(neat): 2222, 758, 690 cm⁻¹

MS(70 eV): 150(M⁺)

(2) A solution of 2.5 g of the above-mentioned compound, 3.79 g ofdimethyl 2-acetamidomalonate and 1.43 g of sodium ethoxide in 50 ml ofethanol was refluxed under heating for 3 hours under a nitrogenatmosphere. Water (20 ml) was added thereto to stop the reaction and themixture was extracted with ethyl acetate. The extract was dried overanhydrous sodium sulfate and the solvent was distilled away. The residuewas purified by silica gel column chromatography (ethylacetate:hexane=1:7-1:2) to give 2.5 g of diethyl2-acetamido-2-(3-phenyl-2-propynyl)malonate as white crystals.

melting point=94°-96.5° C.

Rf: 0.38 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.28 (6H, t, J=7.5 Hz), 2.08 (3H, s), 3.49 (2H,s), 4.30 (4H, q, J=7.5 Hz), 6.98 (1H, br.s), 7.16-7.49 (5H, m)

IR(KBr): 3260, 1747, 1643, 1197 cm⁻¹

MS(70 eV): 331(M⁺)

(3) A solution (50 ml) of 1.8 g of the above-mentioned compound and 0.47g of lithium borohydride in tetrahydrofuran was refluxed under heatingfor 1.5 hours under a nitrogen atmosphere. After cooling, the mixturewas neutralized with 8 ml of a 1N aqueous hydrochloric acid solution andevaporated to dryness. Acetic anhydride (4 ml) and 30 ml of pyridinewere added to the residue and the mixture was stirred at roomtemperature for 2.5 hours. The reaction mixture was poured into icewater and extracted with chloroform. The extract was washed with 1Nhydrochloric acid and saturated brine in order and dried. The solventwas distilled away and the residue was purified by silica gel columnchromatography (ethyl acetate: hexane=2:1) to give 430 mg of2-acetamido-1,3-diacetoxy-2-(3-phenyl-2-propynyl)propane as a colorless,oily substance.

Rf: 0.64 (ethyl acetate)

¹ H-NMR (CDCl₃ /TMS) δ: 1.98 (3H, s), 2.07 (6H, s), 3.09 (2H, s), 4.47(4H, s), 5.95 (1H, br.s), 7.18-7.48 (5H, m)

IR(neat): 3293, 2135, 1745, 1662 cm⁻¹

MS(70 eV): 331(M⁺)

EXAMPLE 19

2-Acetamido-1,3-diacetoxy-2-(3-phenyl-2-propynyl)propane (430 mg) wasdissolved in 8 ml of methanol and 8 ml of a 1N aqueous sodium hydroxidesolution was added thereto. The mixture was refluxed under heating for 2hours. The solvent was distilled away and the residue was purified bysilica gel column chromatography (methanol:chloroform=1:50-1:7) to give230 mg of 2-amino-2-(3-phenyl-2-propynyl)-1,3-propanediol as a paleyellow, amorphous-like solid.

Rf: 0.20 (methanol:chloroform: 1:5)

IR(KBr): 3281, 2932, 1558, 1049 cm⁻¹

EXAMPLE 20

(1) A solution of 1.1 g of 4-(4-butylphenyl)butanol, 1.05 g of tosylchloride, 0.48 ml of pyridine and a catalytic amount ofdimethylaminopyridine in dichloromethane was allowed to stand at roomtemperature overnight. The reaction mixture was poured into 50 ml of icewater and extracted with chloroform. The extract was dried overanhydrous sodium sulfate and the solvent was distilled away. The residuewas purified by silica gel column chromatography (ethyl acetate:hexane:1:6) to give 1.2814 g of 4-(4-butylphenyl)butyl p-toluenesulfonate as acolorless, oily substance.

¹ H-NMR (CDCl₃ /TMS) δ: 0.96 (3H, t, J=7 Hz), 1.50-2.00 (8H, m), 2.48(3H, s), 2.40-2.75 (4H, m), 4.08 (2H, t, J=6 Hz), 7.07 (4H, m), 7.36(2H, d, J=8 Hz), 7.83 (2H, d, J=8 Hz)

IR: 2956, 2929, 2858, 1361 cm⁻¹

MS: 360(M⁺)

(2) The above-mentioned compound (1.2138 g) and 0.606 g of sodium iodidewere dissolved in 34 ml of 2-butanone and the mixture was refluxed underheating for 4 hours. The mixture was poured into 100 ml of ice water andextracted with ethyl acetate. The extract was dried over anhydroussodium sulfate and the solvent was distilled away. The residue waspurified by silica gel column chromatography (ethyl acetate:hexane=1:9)to give 0.953 g of 4-(4-butylphenyl)-1-iodobutane as a red, oilysubstance.

Rf: 0.75 (ethyl acetate:hexane=1:5)

¹ H-NMR (CDCl₃ /TMS) δ: 0.92 (3H, t, J=7 Hz), 1.10-2.05 (8H, m), 2.59(4H, t, J=7.5 Hz), 3.20 (2H, t, J=7 Hz), 7.07 (5H, s)

(3) A solution of 953.4 mg of the above-mentioned compound, 687.7 mg ofdiethyl 2-acetamidomalonate and 260 mg of sodium ethoxide in 10 ml ofethanol was refluxed under heating for 3 hours under a nitrogenatmosphere. The mixture was poured into 100 ml of ice water andextracted with ethyl acetate. The extract was dried over anhydroussodium sulfate and the solvent was distilled away. The residue waspurified by silica gel column chromatography (ethylacetate:hexane=1:3-1:2) to give 480 mg of diethyl 2-acetamido-2-4-(4-butylphenyl)butyl!malonate as white crystals.

melting point=60°-61° C.

Rf: 0.38 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 0.93 (3H, t, J=6 Hz), 1.24 (3H, t, J=7 Hz),1.09-1.85 (8H, m), 2.02 (3H, s), 2.35 (2H, m), 2.58 (4H, t, J=7.5 Hz),4.25 (2H, q, J=6 Hz), 6.75 (1H, br.s), 7.07 (4H, s)

IR: 3270, 2930, 2850, 1740, 1640 cm⁻¹

MS: 405(M+), 290 elemental analysis: calculated C 68.12, H 8.70, N 3.45found C 68.25, H 8.69, N 3.55

(4) A solution (15 ml) of 450 mg of the above-mentioned compound and 100mg of lithium borohydride in tetrahydrofuran was refluxed under heatingfor 2 hours under a nitrogen atmosphere. The mixture was neutralizedwith 2.5 ml of a 2N aqueous hydrochloric acid solution and dried tosolidness. Acetic anhydride (2 ml) and 4 ml of pyridine were added tothe residue and the mixture was stirred at room temperature overnight.The reaction mixture was poured into ice water and extracted with ethylacetate. The extract was washed with 2N hydrochloric acid, a saturatedsodium bicarbonate solution and saturated brine in order and dried. Thesolvent was distilled away and the residue was purified by silica gelcolumn chromatography (ethyl acetate:hexane=3:1) to give 72.4 mg of2-acetamido-1,3-diacetoxy-2- 4-(4-butylphenyl)butyl!propane as whitecrystals.

melting point=68°-71° C.

Rf: 0.63 (ethyl acetate)

¹ H-NMR (CDCl₃ /TMS) δ: 0.91 (3H, t, J=7 Hz), 1.10-2.40 (10H, m), 1.93(3H, s), 2.06 (6H, s), 2.58 (4H, t, J=7.5 Hz), 4.28 (4H, s), 5.62 (1H,br.s), 7.07 (4H, s)

IR: 3298, 3090, 2931, 2859, 1739, 1652, 1557 cm⁻¹

MS: 405(M⁺)

elemental analysis: calculated C 68.12, H 8.70, N 3.45 found C 67.95, H8.52, N 3.44

EXAMPLE 21

2-Acetamido-1,3-diacetoxy-2- 4-(4-butylphenyl)butyl!propane (66.2 mg)was dissolved in 2 ml of methanol and 2 ml of a 1N aqueous sodiumhydroxide solution was added thereto. The mixture was refluxed underheating for 4 hours. The solvent was distilled away and the residue waspurified by silica gel thin layer chromatography(methanol:chloroform=1:4) to give 24.9 mg of 2-amino-2-4-(4-butylphenyl)butyl!-1,3-propanediol as white crystals.

melting point=92°-94° C.

Rf: 0.15 (methanol:chloroform=1:4)

IR: 3276, 2928, 2858, 1560 cm⁻¹

EXAMPLE 22

(1) 4-(4-Hexylphenyl)butanol (5.0 g) was dissolved in 20 ml of pyridineand 4.88 g of tosyl chloride was added thereto. The reaction mixture wasleft standing at room temperature overnight. The reaction mixture waspoured into ice water and extracted with ethyl acetate. The extract waswashed with 2N hydrochloric acid, a saturated aqueous sodium bicarbonatesolution and saturated brine in order and concentrated. The residue waspurified by silica gel column chromatography (ethyl acetate:hexane=1:7)to give 2.21 g of 4-(4-hexylphenyl)butyl p-toluenesulfonate as acolorless, oily substance.

Rf: 0.35 (ethyl acetate:hexane=1:5)

¹ H-NMR (CDCl₃ /TMS) δ: 0.90 (3H, t, J=6 Hz), 1.09-1.85 (12H, m), 2.46(3H, s), 2.53 (4H, m), 4.06 (2H, t, J=6 Hz), 7.06 (4H, s), 7.34 (2H, d,J=8 Hz), 7.81 (2H, d, J=8 Hz)

IR: 2927, 2856, 1599 cm⁻¹

MS: 388(M+), 216

elemental analysis: calculated C 71.10, H 8.30 found C 71.35, H 8.34

(2) The above-mentioned compound (2.21 g) and 1.02 g of sodium iodidewere dissolved in 57 ml of 2-butanone and the mixture was refluxed underheating for 2 hours. The reaction mixture was poured into ice water andextracted with ethyl acetate. The extract was washed with saturatedbrine, and dried and concentrated. The residue was purified by silicagel column chromatography (ethyl acetate:hexane=1:9) to give 1.765 g of4-(4-hexylphenyl)-1-iodobutane as a colorless, oily substance.

Rf: 0.43 (ethyl acetate:hexane=1:5)

¹ H-NMR (CDCl₃ /TMS) δ: 0.90 (3H, t, J=6 Hz), 1.05-2.05 (12H, m), 2.60(4H, m), 3.21 (2H, t, J=7 Hz), 7.10 (4H, s)

MS: 344(M+), 273, 175

elemental analysis: calculated C 55.82, H 7.32 found C 55.81, H 7.32

(3) A solution of 1.6806 g of the above-mentioned compound, 1.1133 g ofdiethyl 2-acetamidomalonate and 523 mg of sodium ethoxide in 20 ml ofethanol was refluxed under heating for 4.5 hours under a nitrogenatmosphere. The reaction mixture was poured into ice water and extractedwith ethyl acetate. The extract was dried and concentrated. The residuewas purified by silica gel column chromatography (ethylacetate:hexane=1:3) to give 870 mg of diethyl 2-acetamido-2-4-(4-hexylphenyl)butyl!malonate as white crystals.

melting point=57°-58° C.

Rf: 0.42 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 0.91 (3H, t, J=6 Hz), 1.24 (6H, t, J=7 Hz),1.08-1.90 (12H, m), 2.02 (3H, s), 2.35 (2H, m), 2.58 (4H, t, J=7 Hz),4.23 (4H, q, J=7 Hz), 6.74 (1H, br.s), 7.07 (4H, s)

IR: 3270, 2927, 2858, 1746, 1644, 1514 cm⁻¹

MS: 433(M+), 360, 318

elemental analysis: calculated C 69.25, H 9.07, N 3.23 found C 69.44, H8.97, N 3.26

(4) A solution (20 ml) of 840 mg of the above-mentioned compound and 211mg of lithium borohydride in tetrahydrofuran was refluxed under heatingfor 4 hours under a nitrogen atmosphere. The mixture was neutralizedwith 2N hydrochloric acid and the solvent was evaporated to dryness.Acetic anhydride (5.5 ml) and 16 ml of pyridine were added to theresidue and the mixture was stirred at room temperature overnight. Thereaction mixture was treated conventionally and the residue obtained waspurified by silica gel column chromatography (ethyl acetate:hexane=3:1)to give 244.5 mg of 2-acetamido-1,3-diacetoxy-2-4-(4-hexylphenyl)butyl!propane as white crystals.

melting point=61°-64° C.

Rf: 0.71 (ethyl acetate)

¹ H-NMR (CDCl₃ /TMS) δ: 0.88 (3H, t, J=6 Hz), 1.10-1.90 (14H, m), 1.92(3H, s), 2.04 (6H, s), 2.58 (4H, t, J=7 Hz), 4.28 (4H, s), 5.58 (1H,br.s), 7.06 (4H, s)

IR: 3313, 2928, 2856, 1750, 1656 cm⁻¹

MS: 433(M+), 389, 373

elemental analysis: calculated C 69.25, H 9.07, N 3.23 found C 69.26, H9.01, N 3.22

EXAMPLE 23

2-Acetamido-1,3-diacetoxy-2- 4-(4-hexylphenyl)butyl!propane (200.2 mg)was dissolved in 7 ml of methanol and 1N sodium hydroxide was addedthereto. The mixture was refluxed under heating for 5 hours. The solventwas distilled away and the residue obtained was purified by silica gelthin layer chromatography (methanol:chloroform=1:3) to give 79.7 mg of2-amino-2- 4-(4-hexylphenyl)butyl!-1,3-propanediol as white crystals.

melting point=99°-102° C.

Rf: 0.14 (methanol:chloroform=1:4)

IR: 3286, 2927, 2858, 1562, 1514 cm⁻¹

EXAMPLE 24

(1) Concentrated sulfuric acid (18.3 g) was gradually added dropwise to13.94 g of concentrated nitric acid and the mixture was vigorouslyshaken for 10 minutes. To the mixed solution, 10 g of 3-phenylpropylbromide was gradually added dropwise at -20° C. and the mixture wasstirred at -20° C. for 1 hour. The reaction mixture was poured into 500ml of ice water and extracted with ether. The extract was washed anddried, and the solvent was distilled away. The residue was purified bysilica gel column chromatography (ethyl acetate:hexane=1:9) to give 4.5g of 3-(4-nitrophenyl)propyl bromide as a colorless, oily substance.

Rf: 0.33 (ethyl acetate:hexane=1:15)

(2) Sodium (0.68 g) was added to 40 ml of absolute ethanol underice-cooling. The mixture was stirred at room temperature for 30 minutesin a stream of nitrogen to give a sodium ethoxide solution. To thissolution, 1.98 g of diethyl 2-acetamidomalonate was added and 4.8 g ofthe compound of (1) above was dropwise added thereto. The mixture wasrefluxed under heating for 6 hours. The reaction mixture was poured into100 ml of ice water and extracted with ethyl acetate. The extract waswashed and dried, and the solvent was distilled away. The residue waspurified by silica gel column chromatography (ethylacetate:hexane=1:3-1:1) to give 3.0 g of diethyl 2-acetamido-2-3-(4-nitrophenyl)propyl!malonate as a yellow, oily substance.

Rf: 0.51 (ethyl acetate:hexane=1:1)

(3) A solution (50 ml) of 1.0 g of the compound of (2) above and 228 mgof lithium borohydride in tetrahydrofuran was refluxed under heating for2 hours in a stream of nitrogen. The reaction mixture was poured into100 ml of ice water and. extracted with ethyl acetate. The extract waswashed and dried, and the solvent was distilled away. The residue waspurified by silica gel column chromatography (methanol: chloroform=1:9)to give 400 mg of 2-acetamido-2-3-(4-nitrophenyl)propyl!-1,3-propanediol as a yellow, oily substance.

Rf: 0.22 (ethyl acetate)

¹ H-NMR (90 MHz, CDCl₃) δ: 1.38-1.80 (4H, m), 2.00 (3H, s), 2.57-3.04(2H, m), 3.39-4.28 (4H, m), 3.93 (2H, br.s), 6.23-6.58 (1H, m),7.17-7.63 (2H, m), 7:75-8.20 (2H, m)

IR ν: 3301, 2944, 1652, 1519 cm⁻¹

MS(EI): 296(M⁺)

EXAMPLE 25

2-Acetamido-2- 3-(4-nitrophenyl)propyl!-1,3-propanediol (400 mg) wasdissolved in 50 ml of methanol and 6.7 ml of a 1N aqueous-sodiumhydroxide solution was added thereto. The mixture was refluxed underheating for 3 hours and neutralized with dilute hydrochloric acid. Thesolvent was distilled away and chloroform was added to the residue forextraction. The chloroform layer was washed and dried, and the solventwas distilled away. The residue was purified by silica gel columnchromatography (methanol:chloroform=1:4) to give 100 mg of 2-amino-2-3-(4-nitrophenyl)propyl!-1,3-propanediol as a red, oily substance.

Rf: 0.13 (chloroform:methanol=4:1)

¹ H-NMR (90 MHz, CDCl₃) δ: 1.10-2.05 (4H, m), 2.52-3.11 (2H, m),3.19-3.86 (4H, m), 4.65 (4H, br.s), 7.08-7.65 (3H, m), 7.70-8.18 (1H, m)

IR ν: 3359, 2936, 2866, 1524 cm⁻¹

EXAMPLE 26

(1) A 15N aqueous sodium hydroxide solution (2 ml) and a solution (10ml) of 8.0 g of undecyl bromide in ethanol was added to a solution (30ml) of 4.56 g of 3-(3-hydroxyphenyl)propanol in ethanol and the mixturewas stirred at 70° C. for 12 hours. The solvent was distilled away andthe residue was extracted with ethyl acetate. The extract was washedwith saturated sodium hydrogencarbonate and brine, and dried overmagnesium sulfate. The solvent was distilled away and the residue waspurified by silica gel column chromatography (ethylacetate:hexane=1:20-1:3) to give 7.37 g of3-(3-undecyloxyphenyl)propanol as a colorless, oily substance.

¹ H-NMR (90 MHz, CDCl₃) δ: 0.87 (3H, t, J=6 Hz), 1.10-2.08 (20H, m),1.60 (1H, br.s), 2.69 (2H, t, J=6 Hz), 3.55-3.81 (2H, m), 3.94 (3H, t,J=6 Hz), 6.62-6.87 (3H, m), 7.06-7.23 (1H, m)

(2) Carbon tetrabromide (5.68 g) and 4.49 g of triphenylphosphine wereadded to a solution (100 ml) of 5 g of the above-mentioned compound inmethylene chloride and the mixture was stirred at room temperatureovernight. The reaction mixture was poured into ice water and extractedwith methylene chloride. The organic layer was washed and dried, and thesolvent was distilled away. Petroleum ether was added to the residue andinsoluble matters were filtered off. The petroleum ether layer wasdistilled away and the residue was purified by silica gel columnchromatography (ethyl acetate:hexane=1:20) to give 4.6 g of3-(3-undecyloxyphenyl)propyl bromide as a colorless, oily substance.

¹ H-NMR (90 MHz, CDCl₃) δ: 0.83 (3H, t, J=7 Hz), 1.04-1.53 (16H, m),1.55-1.86 (2H, m), 2.14 (2H, m, J=7 Hz), 2.70 (2H, t, J=7 Hz), 3.34 (2H,t, J=7 Hz), 3.90 (2H, t, J=7 Hz), 6.73-6.85 (3H, m), 7.14-7.42 (1H, m)

IR: 2925, 2553, 1583, 1451, 1261 cm⁻¹

(3) Sodium (0.43 g) was added to absolute ethanol (40 ml) underice-cooling and the mixture was stirred at room temperature for 30minutes in a stream of nitrogen to give a 19 mmol solution of sodiumethoxide in ethanol. To this solution, 4.0 g of diethyl2-acetamidomalonate was added and the mixture was stirred at 50° C. for30 minutes in a stream of nitrogen. The compound (4.6 g) of (2) abovewas added thereto at room temperature and the mixture was refluxed underheating for 6 hours. After cooling to room temperature, the mixture wasneutralized with dilute hydrochloric acid and ethanol was distilledaway. The residue was extracted with ethyl acetate. The ethyl acetatelayer was washed and dried, and the solvent was distilled away. Theresidue was purified by silica gel column chromatography (ethylacetate:hexane=1:5-1:1) to give 4.2 g of diethyl 2-acetamido-2-3-(3-undecyloxyphenyl)propyl!malonate as white crystals.

melting point=38°-39° C.

¹ H-NMR (90 MHz, CDCl₃) δ: 0.88 (3H, t, J=7 Hz), 1.12-1.90 (27H, m),2.03 (3H, s), 2.27-2.73 (4H, m), 3.93 (3H, t, J=7 Hz), 4.22 (4H, q, J=7Hz), 6.61-6.87 (3H, m), 7.04-7.22 (1H, m)

IR: 3251, 2917, 1741, 1680 cm⁻¹

MS(EI): 505(M⁺)

(4) A solution (20 ml) of 3.5 g of the compound of (3) above inanhydrous tetrahydrofuran was dropwise added to a solution (50 ml) of1.08 g of lithium aluminum hydride in anhydrous tetrahydrofuran underice-cooling and the mixture was stirred under ice-cooling for 1 hour.The excess lithium aluminum hydride was decomposed and filtered off. Thefiltrate was extracted with ethyl acetate. The ethyl acetate layer waswashed and dried. The solvent was distilled away and the residue waspurified by silica gel column chromatography (ethyl acetate,chloroform:methanol=9:1) to give 1.6 g of 2-acetamido-2-3-(3-undecyloxyphenyl)propyl!-1,3-propanediol as a colorless, oilysubstance.

¹ H-NMR (90 MHz, CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.05-1.45 (16H, m),1.45-1.87 (6H, m), 1.99 (3H, s), 2.47-2.70 (2H, m), 3.64 (4H, dd, J=12Hz, 21 Hz), 3.82 (2H, t, J=6 Hz), 3.79-4.10 (2H, m), 5.89 (1H, br.s),6.60-6.82 (3H, m), 7.03-7.31 (1H, m)

IR: 3307, 2926, 2857, 1652 cm⁻¹

MS(EI): 421 (M⁺)

EXAMPLE 27

2-Acetamido-2- 3-(3-undecyloxyphenyl)propyl!-1,3-propanediol (1.4 g) wasdissolved in 50 ml of methanol and 16.6 ml of a 1N aqueous sodiumhydroxide solution was added thereto. The mixture was refluxed underheating for 3 hours. The mixture was poured into ice water andneutralized with dilute hydrochloric acid. The solvent was distilledaway and chloroform was added to the residue for extraction. Thechloroform layer was washed and dried. The solvent was distilled awayand the residue was recrystallized from diisopropyl ether-hexane to give0.9 g of 2-amino-2- 3-(3-undecyloxyphenyl)propyl!-1,3-propanediol aswhite crystals.

melting point=71°-72° C.

¹ H-NMR (90 MHz, CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.14-1.91 (22H, m),2.20 (4H, br.s), 2.60 (2H, t, J=6 Hz), 3.49 (4H, dd, J=10 Hz, 13 Hz),3.94 (2H, t, J=6 Hz), 6.62-6.86 (3H, m), 7.05-7.21 (1H, m)

IR: 3344, 3289, 3179, 2919, 1610 cm⁻¹

MS(EI): 379(M⁺)

EXAMPLE 28 2-Amino-2- 2-(4-octylphenyl)ethyl!-1,3-propanediol

(1) 2-(4-Octanoylphenyl)ethyl acetate

Aluminum chloride (111.8 g) was added to dichloroethane (500 ml) in astream of nitrogen and the mixture was stirred at room temperature.Then, phenethyl acetate (91.8 g) and decanoyl chloride (100 g) weredropwise added thereto under ice-cooling and the mixture was stirred atroom temperature overnight. The reaction mixture was poured into icewater and extracted with diethyl ether. The ether layer was washed withsaturated brine and dried over anhydrous magnesium sulfate. The solventwas distilled away and the residue was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:20) to give 61.3 g of thesubject compound (yield 38%) as an oily substance.

IR ν Neat max: 2929, 1740, 1685, 1236 cm⁻¹

(2) 2-(4-Octylphenyl)ethyl acetate

Triethylsilane (28.8 ml) was added to a solution (86ml) of theabove-mentioned compound (24.9 g) in trifluoroacetic acid underice-cooling and the mixture Was stirred at room temperature for 2 hours.The solvent was distilled away and thereto was added ice water and thena cool, saturated sodium hydrogencarbonate solution gradually. Themixture was extracted with ethyl acetate and the ethyl acetate layer waswashed and dried over magnesium sulfate. The solvent was distilled awayand the residue obtained was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:20) to give 20.5 g of thesubject compound as an oily substance (yield 87%).

IR ν Neat max: 2927, 2855, 1742, 1237 cm⁻¹

(3) 2-(4-Octylphenyl)ethyl alcohol

Sodium methoxide (11.9 g) was added to a solution of the above-mentionedcompound (30.3 g) in methanol (300 ml) and the mixture was refluxedunder heating for 3 hours. The reaction mixture was concentrated and icewater was added thereto. The mixture was extracted with ethyl acetateand the ethyl acetate layer was washed with a 5% aqueous HCl solutionand saturated brine. The resultant mixture was dried over magnesiumsulfate. The solvent was distilled away and the residue obtained waspurified by silica gel column chromatography (eluent; ethylacetate:hexane=1:15, ethyl acetate) to give 25.0 g of the subjectcompound as an oily substance (yield 97%).

IR ν Neat max: 3357, 2927, 2855, 1467 cm⁻¹

(4) 2-(4-Octylphenyl)ethyl methanesulfonate

Triethylamine (16.4 ml) was added to a solution (500 ml) of theabove-mentioned compound (25 g) in dichloromethane and the mixture wasice-cooled. Methanesulfonyl chloride (13.4 g) was dropwise added theretoand the mixture was stirred at room temperature for 1 hour. The reactionmixture was poured into ice water and extracted with dichloromethane.The dichloromethane layer was washed with a saturated potassiumhydrogencarbonate solution, a 1% saturated aqueous hydrochloric acidsolution and saturated brine and dried over anhydrous magnesium sulfate.The solvent was distilled away and the residue was purified by silicagel column chromatography (eluent; ethyl acetate:hexane=1:19) to give31.6 g of the subject compound as an oily substance (yield 95%).

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.13-1.79 (12H, m), 2.58 (2H,t, J=6 Hz), 2.82 (3H, s), 3.01 (2H, t, J=6 Hz), 4.39 (2H, t, J=6 Hz),7.12 (4H, s)

IR ν Neat max: 2926, 1356, 1174 cm⁻¹

(5) 2-(4-Octylphenyl)ethyl iodide

Sodium iodide (18.13 g) was added to a solution (500 ml) of theabove-mentioned compound (31.5 g) in 2-butanone and the mixture wasrefluxed under heating for 4 hours. The reaction mixture wasconcentrated and poured into ice water. The resultant mixture wasextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over anhydrous magnesium sulfate. The solventwas distilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:20) to give 27.5 gof the subject compound as an oily substance (yield 80%).

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.07-1.79 (12H, m), 2.58 (2H,t, J=6 Hz), 3.01-3.57 (4H, m), 7.11 (4H, s)

IR ν Neat max: 2925, 2853, 1168 cm⁻¹

(6) Diethyl 2-acetamido-2-(4-octylphenyl)ethyl malonate

A solution (80 ml) of sodium ethoxide (8.2 g) in absolute ethanol wasdropwise added to diethyl acetamidomalonate (26 g) in a stream ofnitrogen and the mixture was stirred at 65° C. for 30 minutes. Then, asolution of the above-mentioned compound (13.8 g) in anhydroustetrahydrofuran was dropwise added thereto and the mixture was stirredat 65° C. for 30 minutes. The reaction mixture was concentrated andpoured into ice water.

The resultant mixture was extracted with ethyl acetate. The extract waswashed with saturated brine and dried over anhydrous magnesium sulfate.The solvent was distilled away and the residue was purified by silicagel column chromatography (eluent; ethyl acetate:hexane=1:3) to give10.6 g of the subject compound (yield 61%).

melting point=49°-51° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.14 (6H, t, J=6 Hz), 1.20-1.73(12H, m), 2.95 (3H, s), 2.30-2.83 (6H, m), 4.21 (4H, q, J=6 Hz), 6.74(1H, s), 7.05 (4H, s)

IR ν max: 3257, 2924, 1747, 1643 cm⁻¹

(7) 2-Amino-2- 2-(4-octylphenyl)ethyl!-1,3-propanediol

(a) A solution (100 ml) of the above-mentioned compound (11.55 g) inanhydrous tetrahydrofuran was dropwise added to a solution (260 ml) oflithium aluminum hydride (3.03 g) in anhydrous tetrahydrofuran underice-cooling in a stream of nitrogen and the mixture was stirred at roomtemperature for 2 hours. A saturated aqueous sodium sulfate solution wasadded to the reaction mixture under ice-cooling. The resultant aluminumhydroxide was filtered off and the resultant mixture was dried overanhydrous sodium sulfate. The solvent was distilled away and pyridine(40 ml) was added to the residue. Acetic anhydride (30 ml) was addedthereto under ice-cooling and the mixture was left standing at roomtemperature overnight. The reaction mixture was poured into water-cooled5% hydrochloric acid and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=2:1) togive 8.25 g of 1,3-propanediyl-2-acetamido-2-2-(4-octylphenyl)ethyl!ylidenediacetate as white crystals.

(b) An aqueous solution (100 ml) of lithium hydroxide (7.2 g) was addedto a solution (100 ml) of the above-mentioned diacetate (8.25 g) inmethanol and the mixture was refluxed under heating for 2 hours. Thereaction mixture was concentrated and extracted with ethyl acetate. Theextract was washed with saturated brine and dried over anhydrousmagnesium sulfate. The solvent was distilled away and the residue wasrecrystallized from ethyl acetate to give 4 g of the subject compound,melting point 103°-105° C.

¹ H-NMR (DMSO) δ: 0.86 (3H, t, J=6 Hz), 1.10-1.85 (14H, m), 2.38-2.79(6H, m), 3.39 (4H, s), 7.06 (4H, s), 7.84 (2H, brs)

IR ν: 3354, 2925, 1019 cm⁻¹

EXAMPLE 29 2-Amino-2- 2-(4-octylphenyl)ethyl!-1,3-propanediolhydrochloride

2-Amino-2- 2-(4-octylphenyl)ethyl!-1,3-propanediol (7 g) was dissolvedin ethanol (50 ml) and a 1N hydrochloric acid/ether solution (50 ml) wasadded thereto. The solvent was distilled away and the resultant crystalswere recrystallized from ethanol to give 4.2 g of the subject compound.

melting point=118°-120° C.

¹ H-NMR (DMSO) δ: 0.89 (3H, t, J=6 Hz), 1.07-1.77 (12H, m), 1.82-2.17(2H, 2.42-2.95 (4H, m), 3.80 (4H, s), 5.03 (2H, brs), 7.11 (4H, s), 8.07(3H, brs)

IR ν: 3371, 3265, 2924, 1069 cm⁻¹

EXAMPLE 30 2-Acetamido-1,3-diacetoxy-2-2-(4-octylphenyl)ethyl!-1,3-propane

A solution (100 ml) of diethyl 2-acetamido-2-2-(4-octylphenyl)ethyl!malonate (11.55 g) in anhydrous tetrahydrofuranwas dropwise added to a solution (260 ml) of lithium aluminum hydride(3.0 g) in anhydrous tetrahydrofuran under ice-cooling. The mixture wasstirred for 1 hour under ice-cooling and then at room temperature for 2hours. A saturated aqueous solution of sodium sulfate was dropwise addedunder ice-cooling to decompose lithium aluminum hydride, which was thenfiltered off. The resultant mixture was extracted with ethyl acetate andthe ethyl acetate layer was washed and dried. The solvent was distilledaway and the residue was purified by silica gel column chromatography(chloroform/methanol=9/1) to give crystals of 2-acetamido-2-2-(4-octylphenyl)ethyl!-1,3-propanediol, melting point 66°-68° C. Theobtained compound was dissolved in pyridine (40 ml) and acetic anhydride(30 ml) was added thereto under ice-cooling. The mixture was leftstanding at room temperature overnight. The reaction mixture was pouredinto a 10% aqueous hydrochloric acid solution (500 ml) and extractedwith ethyl acetate. The ethyl acetate layer was washed with an aqueouspotassium hydrogencarbonate solution and saturated brine, and dried overanhydrous magnesium sulfate. The solvent was distilled away and theresidue was purified by silica gel column chromatography (ethylacetate/hexane=2/1) to give 8.25 g of the subject compound yield 71%

melting point=105°-107° C.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t), 1.22-1.29 (10H, m), 1.51-1.61 (2H, 1.93(3H, s), 2.07 (6H, s)., 2.17 (2H, t), 2.54 (2H, t), 2.55 (2H, t), 4.35(4H, s), 5.61. (1H, brs), 7.07 (4H, s)

IR (Nujol) ν: 3310, 2920, 1738, 1652, 1556 cm⁻¹

In the same manner as in the above-mentioned Examples, the followingcompounds can be produced.

EXAMPLE 31 2-Amino-2-hexyl-1,3-propanediol hydrochloride

Rf value: 0.47 (CHCl₃ :MeOH:CH₃ COOH:H₂ O=70:20:6:4)

IR(KBr): 3950, 1560, 1420, 1050 cm⁻¹

EXAMPLE 32 2-Amino-2-octyl-1,3-propanediol hydrochloride

Rf value: 0.48 (CHCl₃ :MeOH:CH₃ COOH:H₂ O=70:20:6:4)

IR(KBr): 3190, 2930, 2850, 1630, 1560, 1410, 1100, 1060, 1020 cm⁻¹

EXAMPLE 33 2-Amino-2-decyl-1,3-propanediol hydrochloride

Rf value: 0.49 (CHCl₃ :MeOH:CH₃ COOH:H₂ O=70:20:6:4)

IR(KBr): 3350, 2920, 2850, 1560, 1470, 1420, 1060 cm⁻¹

EXAMPLE 34 2-Amino-2-dodecyl-1,3-propanediol hydrochloride

IR(KBr): 3260, 3050, 2920, 2850, 1590, 1520, 1470, 1260, 1070, 1050 cm⁻¹

melting point=94.0°-95.5° C.

EXAMPLE 35 2-Amino-2-tridecyl-1,3-propanediol hydrochloride

IR(KBr): 3420, 3320, 2400, 2350, 1620, 1590, 1510, 1465, 1085, 1045,1030, 1000 cm⁻¹

melting point=103.0°-104.0° C.

EXAMPLE 36 2-Amino-2-pentadecyl-1,3-propanediol hydrochloride

IR(KBr): 3430, 3350, 3030, 2920, 2850, 1620, 1590, 1510, 1475, 1080,1055, 1040 cm⁻¹

elemental analysis: calculated C 63.97, H 11.93, N 4.14, O 9.47, Cl10.49 found C 63.91, H 11.96, N 4.17, O 9.45, Cl 10.51

melting point=106.5°-108.0° C.

EXAMPLE 37 2-Amino-2-(2-pentadecynyl)-1,3-propanediol hydrochloride

IR(KBr): 3400, 2920, 2850, 1500, 1470, 1060 cm⁻¹

elemental analysis: calculated C 64.74, H 10.87, N 4.19, O 9.58, Cl10.62 found C 64.34, H 10.95, N 4.13, O 9.57, Cl 10.66

melting point=100.0°-101.0° C.

The instant compound is produced according to the following steps (1)through (6).

(1) Propargyl alcohol (3.00 g) was portionwise added to a mixed solutionof 2.256 g of sodium hydride and 30 ml of dry dimethylformamide underice-cooling under a nitrogen atmosphere. The mixture was stirred at roomtemperature for 30 minutes. The mixture was ice-cooled again and 5.175 gof chloro methyl ether was portionwise added thereto. The mixture wasstirred at room temperature overnight. Then, 4.284 g of sodium hydridewas added thereto under ice-cooling and the mixture was heated to roomtemperature, followed by stirring for 30 minutes. The reaction mixturewas ice-cooled again and a solution of 26.68 g of lauryl bromide in 20ml of dry dimethylformamide was portionwise added thereto. The mixturewas stirred at room temperature overnight. The reaction mixture waspoured into ice water and extracted three times with ethyl acetate. Theethyl acetate layer was washed with saturated brine and dried overmagnesium sulfate anhydride. The solvent was distilled away underreduced pressure and the residue was purified by silica gel columnchromatography to give 12.374 g of 15-methoxymethoxy-13-pentadecyne.

IR(cm⁻¹): 2940, 2850, 1470, 1150, 1005, 1400, 1000, 930

¹ H-NMR (CDCl₃) δ: 0.879 (3H, t, J=6.74 Hz, CH₂ CH₃ ), 1.257 (2OH, br.s,CH₂ ×10), 2.213 (2H, tt, J=6.96, 2.20 Hz, C.tbd.C--CH₂ CH₂), 3.380 (3H,s, OCH₃), 4.204 (2H, t, J=2.20 Hz, OCH₂ C.tbd.C), 4.711 (2H, s, OCH₂ O)

(2) The compound (12,374 g) of (1) above was dissolved in a N solution(230 ml) of hydrochloric acid in methanol and the mixture was heated at65° C. for 1.5 hours. The reaction mixture was concentrated underreduced pressure and the residue was purified by silica gel columnchromatography to give 8.465 g of 2-pentadecynyl alcohol.

melting point=41.5°-42.5° C.

IR(cm⁻¹): 3300, 3200, 2960, 2930, 2850, 1480, 1030

¹ H-NMR (CDCl₃) δ: 0.880 (3H, t, J=6.74 Hz, CH₃), 1.260 (2OH, br.s, CH₂×10), 2.209 (2H, tt, J=6.96, 2.12 Hz, C.tbd.CCH₂), 4,255 (2H, dd,J=2.69, 2.44 Hz, OCH₂)

(3) In a reaction vessel equipped with a calcium chloride tube, 8.465 gof the compound of (2) above was dissolved in 85 ml of dichloromethaneand 15.683 g of carbon tetrabromide and 14.867 g of triphenylphosphinewere added thereto under ice-cooling. The mixture was stirred at 0° C.for 5 minutes. The reaction mixture was concentrated under reducedpressure and the residue was extracted with hexane. The hexane extractobtained was concentrated under reduced pressure and the residue waspurified by silica gel column chromatography to give 7.964 g of2-pentadecynyl bromide.

IR(cm⁻¹): 2930, 2850, 1470, 1420

¹ H-NMR (CDCl₃) δ: 0.880 (3H, t, J=6.43 Hz, CH₃), 1.261 (2OH, br.s, CH₂×10), 2.232 (2H, tt, J=6.96 Hz, 2.36 Hz, C.tbd.C--CH₂), 3.932 (2H, t,J=2.32 Hz, BrCH₂ C.tbd.C)

(4) Diethyl acetamidomalonate (3.327 g) and 1.137 g of sodium ethylatewere dissolved in 50 ml of dry ethanol and the mixture was stirred atroom temperature for 30 minutes under a nitrogen atmosphere. A solutionof 4.000 g of the compound of (3) above in 30 ml of dry ethanol wasadded thereto and the mixture was refluxed for 15 hours. Methanol (50ml) was added to the reaction mixture and the insoluble matters wereremoved. The solvent was distilled away under reduced pressure and theresidue was purified by silica gel column chromatography to give 3.236 gof diethyl 2-acetamido-2-(2-pentadecynyl)malonate.

melting point=43.0°-43.5° C.

IR(cm⁻¹): 3250, 2920, 2850, 1750, 1650, 1540, 1470, 1380, 1300, 1240,1200, 1100, 1080, 1060, 1020, 865

¹ H-NMR (CDCl₃) δ: 0.879 (3H, t, J=6.35 Hz, CH₃), 1.261 (2OH, s, CH₂×10), 1.261 (6H, t, J=7.21 Hz, OCH₂ CH₃ ), 2.057 (3H, s, Ac),2.123-2.077 (2H, m, C.tbd.CCH₂ CH₂), 3.211 (2H, t, J=2.32 Hz, CCH₂--C.tbd.C), 4.253 (2H, q, J=7.08 Hz, OCH₂ CH₃), 4.257 (2H, q, J=7.08 Hz,OCH₂ CH₃), 6.896 (1H, br.s, NH)

(5) In a reaction vessel equipped with a calcium chloride tube, 2.437 gof diethyl 2-acetamido-2-(pentadecynyl)malonate was dissolved in 80 mlof dry tetrahydrofuran and 0.898 g of lithium aluminum hydride was addedthereto under ice-cooling. After heating to a room temperature, themixture was stirred for 30 minutes. Water (3 ml) was added thereto underice-cooling to stop the reaction and the solvent was distilled awayunder reduced pressure. Pyridine (70 ml) and 130 ml of acetic anhydridewere added to the residue and the mixture was stirred at roomtemperature overnight. The reaction mixture was poured into ice waterand extracted three times with ethyl acetate. The ethyl acetate layerwas washed with 1N hydrochloric acid, a saturated aqueous sodiumhydrogencarbonate solution and saturated brine in order and dried overanhydrous magnesium sulfate. The solvent was distilled away underreduced pressure and the residue was purified by silica gel columnchromatography and recrystallized from hexane to give 808 mg of2-acetamido-1,3-diacetoxy-2-(2-pentadecynyl)propane.

melting point=95.5°-96.5° C.

IR(cm⁻¹): 3300, 2930, 2850, 1740, 1650, 1580, 1400, 1380, 1260, 1040

¹ H-NMR (CDCl₃) δ: 0.879 (3H, t, J=6.47 Hz, CH₃), 1.225 (24H, br.s, CH₂×12), 1.980 (3H, s, NAc), 2.089 (6H, s, OAc×2), 2.140 (2H, m, CH₂C.tbd.C--CH₂ CH₂), 2.790 (2H, t, J=2.32 Hz, CH₂ C.tbd.C--CH₂ CH₂), 4.422(4H, s, CH₂ O×2), 5.829 (1H, br.s, NH)

(6) 2-Acetamido-1,3-diacetoxy-2-(2-pentadecynyl)propane (600 mg) wasdissolved in 28 ml of methanol and 7.09 ml of a 1N aqueous sodiumhydroxide solution was added thereto. The mixture was refluxed for 6hours. The reaction mixture was concentrated under reduced pressure andthe residue was dissolved in 20 ml of a solvent (methanol:water=3:7).After adsorption onto Sep-Pak, the residue was eluted with methanol:water=8:2 and the eluate was concentrated. The residue was dissolved inmethanol and the mixture was acidified with hydrochloric acid. Thesolvent was distilled away under reduced pressure to give 343 mg of2-amino-2-(2-pentadecynyl)-1,3-propanediol hydrochloride.

EXAMPLE 38 2-Amino-2-(12-hydroxydodecyl)-1,3-propanediol hydrochloride

IR(KBr): 3350, 2920, 2850, 1500, 1470, 1080, 1050, 1040 cm⁻¹

melting point=138.0°-142.0° C.

The instant compound is produced according to the following steps (1)through (5).

(1) Dodecanediol (23.000 g) was dissolved in 230 ml of drytetrahydrofuran and 40 ml of dichloromethane, and 10 mg ofp-toluenesulfonic acid and 9,578 g of dihydropyran were added thereto.The mixture was stirred at room temperature for a day. Triethylamine(1.0 ml) was added thereto to stop the reaction and the reaction mixturewas concentrated under reduced pressure. The residue was purified bysilica gel column chromatography to give 8.132 g of dodecanediolmonotetrahydropyranyl ether.

IR(cm⁻¹): 3620, 3450, 2930, 2850, 1460, 1360, 1140, 1125, 1080, 1030

(2) The above-mentioned dodecanediol monotetrahydropyranyl ether (7.882g) and 11.437 g of carbon tetrabromide were dissolved in 78 ml ofdichloromethane. Triphenylphosphine (10.843 g) was added thereto underice-cooling and the mixture was stirred at 0° C. for 5 minutes. Thesolvent was distilled away under reduced pressure and the residue waspurified by silica gel column chromatography to give 4.029 g of1-bromo-12-tetrahydropyranyloxydodecane.

IR(cm⁻¹): 2930, 2850, 1460, 1445, 1360, 1140, 1120, 1080, 1020, 980

¹ H-NMR (CDCl₃) δ: 1.274 (16H, br.s), 1.611-1.554 (6H, m), 1.750-1.689(1H, m), 1.888-1.802 (1H, m), 1.852 (2H, qui, J=7.1 Hz), 3.381 (1H, dt,J=9.5, 6.9 Hz), 3.407 (2H, t, J=6.9 Hz), 3.526-3.472 (1H, m), 3.728 (1H,dt, J=9.5, 7.0 Hz), 3.900-3.845 (1H, m), 4.574 (1H, dd, J=4.4, 2.7 Hz)

(3) Diethyl acetamidomalonate (6.996 g) and 3.189 g of sodium ethoxidewere dissolved in 130 ml of dry ethanol and a solution of 10.698 g of1-bromo-12-tetrahydropyranyloxydodecane in 200 ml of dry ethanol wasadded thereto. The mixture was refluxed under heating for 8 hours. Thesolvent was distilled away under reduced pressure and the residue waspurified by silica gel column chromatography to give 5.837 g of diethyl2-acetamido-2-(12-tetrahydropyranyloxydodecyl)malonate.

IR(cm⁻¹): 3450, 2930, 2850, 1740, 1680, 1500, 1380, 1285, 1020

¹ H-NMR (CDCl₃) δ: 1.25 (6H, t, J=7.1 Hz), 1.25 (20H, br.s), 1.61-1.52(6H, m), 1.83-1.71 (2H, m), 2.03 (3H, s), 3.87-3.35 (4H, 4.24 (4H, q,J=7.1 Hz), 4.58 (1H, d.d, J=4.4, 2.4 Hz), 6.77 (1H, br.s)

(4) Diethyl 2-acetamido-2-(12-tetrahydropyranyloxydodecyl)malonate(5.837 g) was dissolved in 13.0 ml of methanol and 2.202 g of sodiumborohydride was gradually added thereto under ice-cooling. The entireamount of sodium hydride was added thereto and the mixture was leftstanding at room temperature for 2 hours. Methanol (30 ml) was addedthereto and the mixture was made to assume weak acidity with 2Nhydrochloric acid. The solvent was distilled away under reducedpressure. Pyridine (100 ml) and acetic anhydride (200 ml) were added tothe residue and the mixture was stirred at room temperature for day andnight. The reaction mixture was poured into ice water and extracted withethyl acetate. The ethyl acetate layer was washed with 1N hydrochloricacid, a saturated aqueous sodium hydrogencarbonate solution and asaturated aqueous sodium chloride solution in order. The mixture wasdried over anhydrous magnesium sulfate and concentrated under reducedpressure. The concentrate was dissolved in 100 ml of methanol and 30 mgof p-toluenesulfonic acid was added thereto. The mixture was stirred atroom temperature for 1 hour. Triethylamine (0.5 ml) was added theretoand the mixture was stirred for 10 minutes, followed by concentrationunder reduced pressure. The concentrate was purified by silica gelcolumn chromatography to give 1.180 g of2-acetamido-1,3-diacetoxy-2-(12-hydroxydodecyl)propane.

melting point=75.0°-76.5° C.

IR(cm⁻¹): 3350, 2930, 2850, 1740, 1630, 1550, 1375, 1270, 1240, 1040

¹ H-NMR (CDCl₃) δ: 1.236 (22H, br.s, CH₂ ×11), 1.843-1.821 (2H, m, CH₂),1.937 (3H, s, NAc), 2.056 (6H, s, OAc×2), 3.608 (2H, br.s, CH₂ OH),4.269 (4H, d.d, J=14.0, 11.5 Hz, CH₂ OAc×2), 5.607 (1H, br.s, NH)

(5) 2-Acetamido-1,3-diacetoxy-2-(12-hydroxydodecyl)propane (500 mg) wasdissolved in 24 ml of methanol and 6.0 ml of a 1N aqueous sodiumhydroxide solution was added thereto. The mixture was refluxed underheating for 6 hours. The reaction mixture was concentrated under reducedpressure and methanol was distilled away. The residue was extracted withethyl acetate, and the extract was washed with water and dried overanhydrous magnesium sulfate. The solvent was distilled away. underreduced pressure and the residue was dissolved in methanol. The mixturewas acidified with hydrochloric acid and the solvent was distilled awayby concentration under reduced pressure. The residue was dried in vacuoto give 103 mg of 2-amino-2-(12-hydroxydodecyl)-1,3-propanediolhydrochloride.

¹ H-NMR (DMSO) δ: 1.23 (22H, s, CH₂ ×11), 3.49-3.40 (6H, m, CH₂ O×3),5.26 (3H, br.s, OH×3) elemental analysis: calculated C 56.94, H 10.99, N4.43, O 16.43, Cl 11.21 found C 56.73, H 10.95, N 4.32, O 16.49, Cl11.51

EXAMPLE 39 2-Acetamido-1,3-diacetoxy-2-hexylpropane

melting point=55°-56° C.

EXAMPLE 40 2-Acetamido-1,3-diacetoxy-2-octylpropane

melting point=79.5°-82° C.

EXAMPLE 41 2-Acetamido-1,3-diacetoxy-2-decylpropane

melting point=70°-72° C.

EXAMPLE 42 2-Acetamido-1,3-diacetoxy-2-dodecylpropane

melting point=75.5°-76.5° C.

EXAMPLE 43 2-Acetamido-1,3-diacetoxy-2-tridecylpropane

melting point=77.0°-78.0° C.

EXAMPLE 44 2-Acetamido-1,3-diacetoxy-2-pentadecylpropane

melting point=82.0°-83.0° C.

EXAMPLE 45 2-Acetamido-1,3-diacetoxy-2-(2-pentadecynyl)propane

IR(KBr): 3300, 2930, 2850, 1740, 1650, 1580, 1400, 1380, 1260, 1040 cm⁻¹

melting point=95.5°-96.5° C.

EXAMPLE 46 2-Amino-2-tetradecyl-1,3-propanediol

IR(KBr): 3300, 3260, 3200, 2930, 2860, 1580, 1480, 1070, 105 cm⁻¹

melting point=68.5°-69.5° C.

EXAMPLE 47 2-(N-Ethylamino)-2-octadecyl-1,3-propanediol

IR(KBr): 3360(br), 2920, 2850, 1470, 1070 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 3.530 (2H, d, J=11.4 Hz), 3,472 (2H, d, J=11.4Hz), 2.545 (2H, q, J=7.2 Hz), 2.5 (2H, br.s), 1.252 (34H, m), 1,121 (3H,t, J=7.0 Hz), 0.879 (3H, t, J=6.6 Hz)

melting point=65.0°-67.0° C.

EXAMPLE 48 2-(N,N-Dimethylamino)-2-tetradecyl-1,3-propanediol

IR(KBr): 3530, 3050(br), 2920, 2850, 1470, 1060, 1040, 1030 cm⁻¹

melting point=51°-52° C.

EXAMPLE 49 2-Amino-2-(4-tetradecenyl)-1,3-propanediol hydrochloride

The instant compound is produced by the following steps (1) through (6).

(1) Diethyl acetamidomalonate (6.0 g) was dissolved in 50 ml ofdehydrated ethanol and 2.26 g of sodium ethoxide and 5.22 g of5-bromo-1-pentene were added thereto. The mixture was refluxed under anitrogen atmosphere overnight. The reaction mixture was neutralized andconcentrated. The concentrate was purified by silica gel columnchromatography using hexane-ethyl acetate (5:1→2:1) as an eluent to give4.871 g of colorless, oily diethyl 2-acetamido-2-pentenylmalonate.

IR ν max (CHCl₃): 3450, 3000, 2950, 1740, 1680, 1500, 1480, 1280, 1200,1100, 1020, 920, 860 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 1.25 (2H, m), 1.255 (GH, t, J=7.2 Hz), 2,044(2H, m), 2.040 (3H, s), 2.336 (2H, m), 4.246 (4H, q, J=7.2 Hz), 4.990(1H, dd, J=1.8, 17.2 Hz), 5.013 (1H, dd, J=1.8, 10.6 Hz), 5.758 (1H,ddt, J=6.2, 10.6, 17.2 Hz), 6.789 (1H, s)

(2) Diethyl 2-acetamido-2-pentenylmalonate (4.0 g) was dissolved in 210ml of acetone and 3.3 g of N-methylmorpholine-N-oxide and 36 ml of a 1%aqueous osmium tetraoxide solution were added thereto. The mixture wasstirred at room temperature for 2 hours. A solution of 700 mg of sodiumsulfite in 20 ml of water was added thereto and the mixture was stirredfor 15 minutes. The reaction mixture was concentrated and subjected tosilica gel column chromatography using chloroform/methanol (10:1) as aneluent and a fraction having an Rf value: 0.3 (chloroform:methanol=10:1)was concentrated. The residue was dissolved in 630 ml of 1,4-dioxane and70 ml of a 0.2 M aqueous meta-sodium periodate solution was addedthereto. The mixture was stirred at room temperature for 2 hours. Thereaction mixture was filtrated, concentrated, extracted with ethylacetate and washed with water. The hexane layer was dried andconcentrated to give 4.17 g of colorless, oilydiethyl-2-acetamido-2-(4-formylbutyl)malonate.

Rf value=0.4 (chloroform:methanol=10:1)

(3) Decane bromide (7.0 g) and 10 g of triphenylphosphine were stirredat 120° C. under a nitrogen atmosphere for 8 hours. The mixture wasrecrystallized from acetone-ether to give 14.4 g of colorless,crystalline decyltriphenylphosphonium bromide.

IR ν max (CHCl₃): 2920, 2850, 1440, 1120, 1000, 680 cm⁻¹

(4) Decyltriphenylphosphonium bromide (10.85 g) was dissolved in 100 mlof dry tetrahydrofuran. Under an argon atmosphere, 13 ml of a 1.6 Mn-butyl lithium/hexane solution was dropwise added thereto and themixture was stirred for 15 minutes. The mixture was cooled to -78° C.and a solution of diethyl 2-acetamido-2-(4-formylbutyl)malonate (4.17g)/dry tetrahydrofuran (50 ml) was dropwise added thereto and themixture was stirred at 78° C. for 40 minutes under an argon atmosphere.Under the same conditions, a solution of t-butanol (3.3ml)/tetrahydrofuran (15 ml) was dropwise added thereto and the mixturewas stirred at room temperature under an argon atmosphere for 1.5 hours.The reaction mixture was diluted with ether and washed with water. Theorganic layer was dried and concentrated. The concentrate was purifiedby silica gel column chromatography using hexane-acetic acid (5:1→5:2)as an eluent to give 2.1 g of colorlegs, oily diethyl2-acetamido-2-(4-tetradecenyl)malonate.

IR ν max (CHCl₃): 3450, 2940, 2850, 1740, 1680, 1500, 1380, 1280, 1200,1100, 1020, 860 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 0.88 (3H, t, J=6.6 Hz), 1.257 (16H, m), 1.255(6H, t, J=7.08 Hz), 2.010 (4H, m), 2.066 (3H, s), 2.334 (2H, m), 4.243(4H, q, J=7.08 Hz), 5.273 (1H, dt, J=5.4, 10.8 Hz), 5.376 (1H, dr,J=5.4, 10.8 Hz), 6.775 (1H, s)

(5) Diethyl 2-acetamido-2-(4-tetradecenyl)malonate (807 mg) wasdissolved in 25 ml of dry tetrahydrofuran and 297 mg of lithium aluminumhydride was added thereto under ice-cooling. The mixture was stirred atroom temperature for 1.5 hours. Water (0.544 ml) was added thereto underice-cooling and the mixture was stirred at room temperature for 30minutes. The reaction mixture was concentrated and an appropriate amountof pyridine-acetic anhydride was added to the residue. The mixture wasstirred at room temperature overnight. The reaction mixture was added toice, extracted with ethyl acetate and washed with 1N hydrochloric acid,a saturated aqueous sodium hydrogencarbonate solution and a saturatedaqueous sodium chloride solution. The ethyl acetate layer was dried,concentrated and purified by silica gel column chromatography usinghexane-ethyl acetate (3:1→2:1) as an eluent to give 537 mg of colorless,powdery 2-acetamido-1,3-diacetoxy-2-(4-tetradecenyl)propane.

IR ν max (CHCl₃): 3430, 2920, 2850, 1740, 1680, 1500, 1370, 1280, 1180,1090, 1010, 855 cm⁻¹

(6) 2-Acetamido-1,3-diacetoxy-2-(4-tetradecenyl)propane (450 mg) wasdissolved in 27 ml of methanol and 9 ml of a 1N aqueous sodium hydroxidesolution was added thereto. The mixture was refluxed under a nitrogenatmosphere for 8 hours. The reaction mixture was neutralized withhydrochloric acid and concentrated. Water was added to the concentrateand the mixture was subjected to chromatography using Sep-Pak(C₁₈)(trade mark) and elution with methanol. The methanol eluate wasconcentrated to give 332 mg of pale yellow, oily2-amino-2-(4-tetradecenyl)1,3-propanediol hydrochloride.

IR ν max (KSr): 3400(br), 2920, 2850, 1590, 1500, 1470, 1050, 1040 cm⁻¹

Rf value: 0.6 (chloroform:methanol:acetic acid:water=70:20:6:4)

EXAMPLE 50 2-Amino-1,3-diacetoxy-2-octadecylpropane

IR(CHCl₃): 3400(br), 2930, 2850, 1740, 1470, 1380, 1240, 1040 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 4.014 (2H, d, J=11.0 Hz), 3,938 (2H, d, J=11.0Hz), 2.089 (6H, s), 1.255 (34H, m), 0,879 (3H, t, J=6.6 Hz)

The instant compound is produced as follows.

(1) 2-Amino-1,3-propanediol hydrochloride (7 g) was suspended in 150 mlof N,N-dimethylformamide, and 3.8 g of triethylamine and 5.4 g ofdi-t-butyldicarbonate were added thereto. The mixture was stirred at 50°C. for 5 hours. Under ice-cooling, water was added to the reactionmixture and the mixture was stirred. The resultant precipitate wascollected by filtration. The precipitate was recrystallized fromhexane-ethyl acetate (5:1) to give 6.79 g of colorless, crystalline2-octadecyl-2-(N-t-butoxycarbonylamino)-1,3-propanediol.

IR ν max (KBr): 3400(br), 3300, 2920, 2850, 1680, 1560, 1300, 1180, 1020cm⁻¹

(2) The compound (4 g) of (1) above was dissolved in 15 ml of pyridineand 50 ml of acetic anhydride and the mixture was refluxed at roomtemperature overnight. The reaction mixture was poured into ice water,extracted with ethyl acetate and washed with 1N hydrochloric acid, asaturated aqueous sodium hydrogencarbonate solution and a saturatedaqueous sodium chloride solution. After dehydration, the reactionmixture was concentrated to give 4.8 g of colorless, oily1,3-diacetoxy-2-(N-t-butoxycarbonylamino)propane.

IR ν max (CHCl₃): 3460, 2930, 2850, 1740, 1690(sh), 1510, 1470, 1380,1240, 1160, 1040 cm⁻¹

(3) The compound (4.8 g) of (2) above was dissolved in 10 ml oftrifluoroacetic acid and the mixture was left standing at roomtemperature for 15 minutes. The reaction mixture was diluted with ethylacetate and washed with a saturated aqueous sodium hydrogencarbonatesolution and saturated sodium chloride. The ethyl acetate layer wasdehydrated and concentrated to give 3.83 g of colorless, oily2-amino-1,3-diacetoxy-2-octadecylpropane.

EXAMPLE 51 1,3-Diacetoxy-2-octadecyl-2-(N-pentanoylamino)propane

IR(CHCl₃): 3450, 3400, 2920, 2850, 1740, 1680, 1520, 1460, 1380, 1240,1020 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 5.599 (1H, s), 4.330 (2H, d, J=11.6 Hz), 4.271(2H, d, J=11.6 Hz), 2.150 (2H, t, J=7.2 Hz), 2.078 (6H, s), 1.6 (4H, m),1.251 (34H, m), 0.918 (3H, t, J=7.4 Hz), 0.879 (3H, t, J=6.8 Hz)

EXAMPLE 52 2-Octadecyl-2-(N-pentanoylamino)-1,3-propanediol

IR(KBr): 3420, 3350(br), 2920, 2850, 1650, 1520, 1460, 1030 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 5.840 (1H, s), 4.021 (2H, br.s), 3.803 (2H, d,J=11.4 Hz), 3.559 (2H, t, J=11.4 Hz), 2.231 (2H, t, J=7.8 Hz); 1.6 (4H,m), 1.251 (34H, m), 0.928 (3H, t, J=7.4 Hz), 0.878 (3H, t, J=6.6 Hz)

melting point=73.0°-73.5° C.

The instant compound is produced as follows.

(1) 2-Amino-1,3-diacetoxy-2-octadecylpropane (1.0 g) was dissolved in 50ml of dry ether and 425 mg of N,N-dimethylaniline and 500 mg ofpentanoyl chloride were added thereto. The mixture was stirred at roomtemperature under a nitrogen atmosphere for 6 hours. The reactionmixture was diluted with ethyl acetate and washed with 1N hydrochloricacid, a saturated aqueous sodium hydrogencarbonate solution and asaturated aqueous sodium chloride solution. The organic layer was driedand the resultant mixture was concentrated. The concentrate was purifiedby silica gel column chromatography using hexane-ethyl acetate (5:1→2:1)as an eluent to give 1.036 g of colorless, oily1,3-diacetoxy-2-octadecyl-2-(N-pentanoylamino)propane.

IR ν max (CHCl₃): 3450, 3400, 2920, 2850, 1740, 1680, 1520, 1460, 1380,1240, 1020 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 0.879 (3H, t, J=6.8 Hz), 0.918 (3H, t, J=7.4Hz), 1.251 (34H, m), 1.6 (4H, m), 2.078 (6H, s), 2.150 (2H, t, J=7.2Hz), 4.271 (2H, d, J=11.6 Hz), 4.330 (2H, d, J=11.6 Hz), 5.599 (1H, s)

(2) 1,3-Diacetoxy-2-octadecyl-2-(N-pentanoylamino)propane (400 mg) wasdissolved in 8 ml of methanol and 17 mg of a 28% sodiummethoxide-methanol solution was added thereto. The mixture was stirredat room temperature for 1 hour. Concentrated hydrochloric acid-methanol(1:11, 0.088 ml) was added thereto and the mixture was concentrated. Theconcentrate was subjected to silica gel column chromatography usingchloroform-methanol (30:1) as an eluent. The resultant crystals wererecrystallized from chloroform-hexane to give 312 mg of colorless,crystalline 2-octadecyl-2-(N-pentanoylamino)-1,3-propanediol.

EXAMPLE 53 2-Octadecyl-2-(N-pentylamino)-1,3-propanediol

IR(KBr): 3470(br), 2930, 2850, 1480, 1060 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 3.990 (3H, br.s), 3.707 (2H, d, J=12.8 Hz),3.643 (2H, d, J=12.8 Hz), 2.686 (2H, t, J=7.8 Hz), 1.252 (4OH, m), 0.908(3H, t, J=7.0 Hz), 0.879 (3H, t, J=6.6 Hz)

melting point=53.0°-54.0° C.

The instant compound is produced as follows.

1,3-Diacetoxy-2-octadecyl-2-(N-pentanoylamino)propane (400 mg) wasdissolved in 30 ml of dry ether and 150 mg of lithium aluminum hydridewas added thereto under ice-cooling. The mixture was stirred at roomtemperature for 3 hours. The reaction mixture was concentrated and 20 mlof dry tetrahydrofuran was added thereto. Under ice-cooling, 0.15 ml ofwater, 0.15 ml of a 15% aqueous sodium hydroxide solution and 0.45 ml ofwater were added-in order and the reaction mixture was filtered. Thefiltrate was concentrated and purified by silica gel columnchromatography using chloroform-methanol-acetic acid(19:1:0.1→10:1:0.05) as an eluent to give 153 mg of colorless, powdery2-octadecyl-2-(N-pentylamino)-1,3-propanediol.

EXAMPLE 54 2-(N-Decanoylamino)-1,3-diacetoxy-2-octadecylpropane

¹ H-NMR (CDCl₃ /TMS) δ: 5.594 (1H, s), 4.828 (2H, d, J=12.0 Hz), 4.269(2H, d, J=12.0 Hz), 2.140 (2H, t, J=7.2 Hz), 1.6 (2H, m), 1.252 (46H,m), 0.878 (6H, t, J=6.8 Hz)

Rf value: 0.5 (EtOAc:C₆ H₁₄ =1:2)

EXAMPLE 55 2-(N-Decanoylamino)-2-Octadecyl-1,3-propanediol

IR(KBr): 3350, 3100, 2920, 2850, 1640, 1560, 1480, 1080 cm⁻¹

melting point=71.5°-72.5° C.

EXAMPLE 56 2-(N-Decylamino)-2-octadecyl-1,3-propanediol

IR(KBr): 3350(br), 2920, 2850, 1470, 1060 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 3.562 (2H, d, J=12.8 Hz), 3.498 (2H, d, J=12.8Hz), 2.741 (3H, br.s), 2.536 (2H, t, J=7.2 Hz), 1.525 (2H, 1.251 (48H,m), 0.879 (6H, t, J=6.8 Hz)

melting point=48.0°-49.5° C.

EXAMPLE 57 1,3-Diacetoxy-2-(N,N-dimethylamino)-2-octadecylpropane

¹ H-NMR (CDCl₃ /TMS) δ: 4.208 (2H, d, J=11.4 Hz), 4.071 (2H, d, J=11.4Hz), 2.359 (6H, s), 2.070 (6H, s), 1.252 (34H, m), 0.878 (3H, t, J=6.8Hz)

Rf value: 0.4 (EtOAc:C₆ H₁₄ =3:2)

EXAMPLE 58 2-(N,N-Dimethylamino)-2-octadecyl-1,3-propanediol

IR(KBr): 3540, 3100(br), 2920, 2850, 1470, 1060, 1040 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 3.715 (2H, d, J=10.8 Hz), 3.632 (2H, d, J=10.8Hz), 3.040 (2H, br.s), 2.412 (6H, s), 1.253 (34H, m), 0.880 (3H, t,J=6.8 Hz)

melting point=63.5°-64.5° C.

The instant compound is produced as follows.

(1) 2-Amino-1,3-diacetoxy-2-octadecylpropane (700 mg) was dissolved in35 ml of acetonitrile and 1.38 g of 37% formaldehyde and 330 mg ofsodium cyanoborohydride were added thereto. The mixture was stirred atroom temperature for 1 hour. Acetic acid (0.265 ml) was added theretoand the mixture was stirred at room temperature for 1 hour. The reactionmixture was concentrated and purified by silica gel columnchromatography using hexane-ethyl acetate (4:1→3:1) as an eluent to give436 mg of colorless, oily1,3-diacetoxy-2-(N,N-dimethylamino)-2-octadecylpropane.

¹ H-NMR (CDCl₃ /TMS) δ: 0.878 (3H, t, J=6.8 Hz), 1.252 (34H, m), 2.070(6H, s) 2.359 (6H, s), 4.071 (2H, d, J=11.4 Hz), 4.208 (2H, d, J=11.4Hz)

Rf value: 0.4 (ethyl acetate:hexane=3:2)

(2) The compound (436 mg) of (1) above was dissolved in 15 ml ofmethanol and 37 mg of a 28% sodium methoxide methanol solution was addedthereto. The mixture was stirred at room temperature for 6 hours. Thereaction mixture was concentrated and water was added thereto. Theresultant precipitate was collected by filtration and recrystallizedfrom chloroform-hexane to give 295 mg of colorless, crystalline2-(N,N-dimethylamino)-2-octadecyl-1,3-propanediol.

EXAMPLE 59 2-Amino-2-(cis- or trans-4-tetradecenyl)-1,3-propanediolhydrochloride EXAMPLE 60 2-Amino-2-(3-dodecylthiopropyl)-1,3-propanediolhydrochloride

IR(KBr): 3510, 3450, 3380, 3020, 2920, 2850, 1630, 1530, 1460, 1070,1050 cm⁻¹

¹ H-NMR (CDCl₃ -DMSOd₆ /TMS) δ: 3.78 (2H, d, J=11.8 Hz), 3.68 (2H, d,J=11.8 Hz), 2.5 (4H, m), 1.26 (24H, m), 0.88 (3H, t, J=7.1 Hz)

melting point: 76°-78° C.

The subject compound was prepared as follows:

(1) Dodecylthiol (5 g) was dissolved in 50 ml of dryN,N-dimethylformamide and 1 g of 60% sodium hydride was added theretounder ice-cooling. The mixture was stirred at room temperature for 1hour. Further, a solution of 3.45 g of 3-bromopropanol in 10 ml of dryN,N-dimethylformamide was dropwise added thereto under ice-cooling andthe mixture was stirred at room temperature for 3 hours. The reactionmixture was poured into ice, extracted with ether and washed with 1Nhydrochloric acid, a saturated aqueous sodium hydrogencarbonate solutionand a saturated aqueous sodium chloride solution. The ether layer wasdried and concentrated. The resultant mixture was purified by silica gelcolumn chromatography using hexane-ethyl acetate (10:1→3:1) as an eluentto give 6,071 g of 3-dodecylthiopropanol as a colorless powder.

IR ν max (CHCl₃): 3450(br), 2930, 2850, 1460, 1050 cm⁻¹

(2) 3-Dodecylthiopropanol (3.0 g) was dissolved in 60 ml ofdichloromethane and 7.66 g of carbon tetrabromide and 5.44 g oftriphenylphosphine were added thereto under ice-cooling. The mixture wasstirred under ice-cooling for 15 minutes. The reaction mixture wasconcentrated, and the residue was extracted with hexane. The extract wasconcentrated and purified by silica gel column chromatography usinghexane as an eluent to give 3.255 g of pale yellow, oily3-bromopropyldodecyl sulfide.

Rf value=0.4 (hexane)

(3) Diethyl acetamidomalonate (1.6 g) was dissolved in 30 ml ofdehydrated ethanol and 505 mg of sodium ethoxide and 2 g of3-bromopropyldodecyl sulfide were added thereto. The mixture wasrefluxed under a nitrogen atmosphere overnight. The reaction mixture wasneutralized with concentrated hydrochloric acid-ethanol (1:11) andconcentrated. The concentrate was purified by silica gel columnchromatography using hexane-ethyl acetate (5:1→5:2) as an eluent to give1.722 g of colorless, powdery diethyl2-acetamido-2-(3-dodecylthiopropyl)malonate.

IR ν max (CHCl₃): 3440, 2930, 2850, 1740, 1680, 1500, 1380, 1260, 1100,1020, 860 cm⁻¹

¹ H-NMR (CDCl₃ /TMS) δ: 0.88 (3H, t, J=7.4 Hz), 1.26 (18H, m), 1.26 (6H,t, J=7.3 Hz), 1.57 (4H, m), 2.04 (3H, s), 2.42 (2H, m), 2.47 (2H, t,J=7.3 Hz), 2.48 (2H, t, J=7.3 Hz), 4.25 (4H, q, J=7.4 Hz), 6.78 (1H, s)

(4) Diethyl 2-acetamido-2-(3-dodecylthiopropyl)malonate (1.5 g) wasdissolved in 30 ml of dry tetrahydrofuran and 500 mg of lithium aluminumhydride was added thereto under ice-cooling. The mixture was stirredunder ice-cooling for 30 minutes and at room temperature for 1 hour. Tothe reaction mixture was added 1.0 ml of water under ice-cooling and themixture was stirred for 1 hour and concentrated. Pyridine (5 ml) and 10ml of acetic anhydride were added to the residue, and the mixture wasstirred at room temperature overnight. The reaction mixture was pouredto ice, extracted with ethyl acetate and washed with 1N hydrochloricacid, a saturated aqueous sodium hydrogencarbonate solution and asaturated aqueous sodium chloride solution. The ethyl acetate layer wasdehydrated and concentrated. The concentrate was subjected to silica gelcolumn chromatography using hexane-ethyl acetate (3:1→1:1) as an eluentand recrystallized from hexane to give 852 mg of2-acetamido-1,3-diacetoxy-2-(3-dodecylthiopropyl)propane.

¹ H-NMR (CDCl₃ /TMS) δ: 0.88 (3H, t, J=6.8 Hz), 1.26 (24H, m), 1.96 (3H,s), 2.09 (6H, s), 2.5 (4H, m), 4.30 (4H, s), 5.67 (1H, s)

Rf value=0.4 (ethyl acetate:hexane=7:3)

(5) 2-Acetamido-1,3-diacetoxy-2-(3-dodecylthiopropyl)propane (750 mg)was dissolved in 30 ml of methanol and 10 ml of a 1N aqueous sodiumhydroxide solution was added thereto. The mixture was refluxed under anitrogen atmosphere for 6 hours. The reaction mixture was cooled withice and the resultant precipitate was collected by filtration. Theprecipitate was dissolved in methanol and 3 ml of concentratedhydrochloric acid-methanol (1:11) was added thereto. The mixture wasconcentrated and recrystallized from ethyl acetate-hexane to give 449 mgof colorless, crystalline2-amino-2-(3-dodecylthiopropyl)-1,3-propanediol hydrochloride.

EXAMPLE 61 2-Acetamido-1,3-diacetoxy-2-(3-dodecylthiopropyl)propane

¹ H-NMR (CDCl₃ /TMS) δ: 5.67 (1H, s), 4.30 (4H, s), 2.5 (4H, m), 2.09(6H, s), 1.96 (3H, s), 1.26 (24H, m), 0.88 (3H, t, J=6.8 Hz)

Rf value: 0.4 (EtOAc:C₆ H₁₄ =7:3)

EXAMPLE 62 2-Amino-2-(3,7,11-trimethyldodecyl)-1,3-propanediolhydrochloride EXAMPLE 632-Amino-2-(3,7,11-trimethyl-2,6,10-tridecenyl)-1,3-propanediolhydrochloride EXAMPLE 64 2-Amino-2-(8-oxotetradecyl)-1,3-propanediolhydrochloride EXAMPLE 65 2-Amino-2-(8-hydroxytetradecyl)-1,3-propanediolhydrochloride EXAMPLE 66 2-Amino-2-(2-dodecylaminoethyl)-1,3-propanediolhydrochloride EXAMPLE 672-Amino-2-(2-dodecanoylaminoethyl)-1,3-propanediol hydrochloride EXAMPLE68 2-Amino-2-(11-carboxyundecyl)-1,3-propanediol hydrochloride EXAMPLE69 2-Amino-2-(11-methoxycarbonylundecyl)-1,3-propanediol hydrochlorideEXAMPLE 70 2-Amino-2-(12-acetoxydodecyl)-1,3-propanediol hydrochlorideEXAMPLE 71 2-Acetamido-1,3-diacetoxy-2-(3,7,11-trimethyldodecyl)propaneEXAMPLE 722-Acetamido-1,3-diacetoxy-2-(3,7,11-trimethyl-2,6,10-tridecenyl)propaneEXAMPLE 73 2-Acetamido-1,3-diacetoxy-2-(8-oxotetradecyl)propane EXAMPLE74 2-Acetamido-1,3-diacetoxy-2-(8-hydroxytetradecyl)propane EXAMPLE 752-Acetamido-1,3-diacetoxy-2-(11-methoxycarbonylundecyl)propane EXAMPLE76 2-Amino-2-(2-propynyl)-1,3-propanediol EXAMPLE 772-Amino-2-(2-propenyl)-1,3-propanediol EXAMPLE 78 2 -(N-Methylamino)-2-octadecyl-1,3 -propanediol EXAMPLE 792-(N,N-Dimethylamino)-2-octadecyl-1,3-propanediol EXAMPLE 802-(N-Octadecylamino)-2-octadecyl-1,3-propanediol EXAMPLE2-(N,N-Dioctadecylamino)-2-octadecyl-1,3-propanediol EXAMPLE 822-(N-Octadecanoylamino)-2-octadecyl-1,3-propanediol EXAMPLE 832-Amino-2-decyl-1,3-propanediol EXAMPLE 842-Amino-2-dodecyl-1,3-propanediol EXAMPLE 852-Acetamido-2-octadecyl-1,3-propanediol EXAMPLE 862-Amino-2-(2-octadecynyl)-1,3-propanediol EXAMPLE 872-Amino-2-(2-octadecenyl)-1,3-propanediol EXAMPLE 882-Amino-2-(4-phenylbutyl)-1,3-propanediol EXAMPLE 892-Amino-2-(5-phenylpentyl)-1,3-propanediol EXAMPLE 902-Amino-2-(2-phenylpropyl)-1,3-propanediol EXAMPLE 91 2-Amino-2-8-(4-hexylphenyl)octyl!-1,3-propanediol EXAMPLE 92 2-Amino-2-4-(4-decylphenyl)butyl!-1,3-propanediol EXAMPLE 93 2-Amino-2-4-(4-pentyloxyphenyl)butyl!-1,3-propanediol EXAMPLE 94 2-Amino-2-4-(4-bromophenyl)butyl!-1,3-propanediol EXAMPLE 95 2-Amino-2-3-(2,4-dinitrophenyl)propyl!-1,3-propanediol EXAMPLE 96 2-Amino-2-3-(4-aminophenyl)propyl!-1,3-propanediol EXAMPLE 97 2-Amino-2-3-(4-decyloxyphenyl)-2-propenyl!-1,3-propanediol EXAMPLE 982-Amino-2-(14-fluorotetradecyl)-1,3-propanediol hydrochloride, meltingpoint=92°-94° C. EXAMPLE 992-Acetamido-1,3-diacetoxy-2-(14-fluorotetradecyl)propane, meltingpoint=82°-84° C. EXAMPLE 1002-Amino-2-(9-pentyloxynonyl)-1,3-propanediol 1/5 hydrate, meltingpoint=32°-33° C. EXAMPLE 1012-Acetamido-1,3-diacetoxy-2-(9-pentyloxynonyl)propane, meltingpoint=62°-64° C. EXAMPLE 102 2-Amino-2-(8-hexyloxyoctyl)-1,3-propanediolhydrochloride, melting point=66°-67° C. EXAMPLE 1032-Acetamido-1,3-diacetoxy-2-(8-hexyloxyoctyl)propane, meltingpoint=66°-69° C. EXAMPLE 1042-Amino-2-(7-heptyloxyheptyl)-1,3-propanediol hydrochloride, meltingpoint=59°-61° C. EXAMPLE 1052-Acetamido-1,3-diacetoxy-2-(7-heptyloxyheptyl)propane, meltingpoint=53°-55° C. EXAMPLE 106 2-Amino-2-(6-octyloxyhexyl)-1,3-propanediolhydrochloride, melting point=58°-62° C. EXAMPLE 1072-Acetamido-1,3-diacetoxy-2-(6-octyloxyhexyl)propane, meltingpoint=47°-50° C. EXAMPLE 108 2-Amino-2-(2-phenylethyl)-1,3-propanediolhydrochloride, melting point=156°-157° C. EXAMPLE 1092-Acetamido-1,3-diacetoxy-2-(2-phenylethyl)propane, meltingpoint=116°-117° C. EXAMPLE 110 2-Amino-2-(3-phenylbutyl)-1,3-propanediolhydrochloride 1/5 hydrate,

melting point=111°-118° C.

EXAMPLE 111 2-Acetamido-1,3-diacetoxy-2-(3-phenylbutyl)propane, meltingpoint=98°-99° C. EXAMPLE 112 2-Amino-2-(6-phenylhexyl)-1,3-propanediol,

melting point=77°-79° C.

EXAMPLE 113 2-Acetamido-1,3-diacetoxy-2-(6-phenylhexyl)propane, meltingpoint=58°-59° C. EXAMPLE 114 2-Amino-2-(10-phenyldecyl)-1,3-propanediol,

melting point=87°-88.5° C.

EXAMPLE 115 2-Acetamido-1,3-diacetoxy-2-(10-phenyldecyl)propane,

IR; 3301, 2928, 2855, 1747, 1661, 1552 cm⁻¹

EXAMPLE 116 2-Amino-2- 6-(3-phenylpropyloxy)hexyl!-1,3-propanediol 1/4hydrate, melting point=66°-67° C. EXAMPLE 1172-Acetamido-1,3-diacetoxy-2- 6-(3-phenylpropyloxy)hexyl!propane,

IR; 3418, 1735, 1655, 1026 cm⁻¹

EXAMPLE 118 2-Amino-2- 8-(phenylmethyloxy)octyl!-1,3-propanediolhydrochloride, melting point=87°-88° C. EXAMPLE 1192-Acetamido-1,3-diacetoxy-2- 8-(phenylmethyloxy)octyl!propane,

IR; 3308, 1740, 1660, 1240 cm⁻¹

EXAMPLE 120 2-Amino-2- 3-(4-heptylcyclohexyl)propyl!-1,3-propanediol,melting point=65°-66° C. EXAMPLE 121 2-Acetamido-1,3-diacetoxy-2-3-(4-heptylcyclohexyl)propyl!propane, melting point=53°-55° C. EXAMPLE122 2-Amino-2- 4-(4-butylcyclohexyl)butyl!-1,3-propanediol hydrochloride1/5 hydrate,

melting point=96°-99° C.

EXAMPLE 123 2-Acetamido-1,3-diacetoxy-2-4-(4-butylcyclohexyl)butyl!propane, melting point=66°-69° C. EXAMPLE 1242-Amino-2-(4-nonylphenylmethyl)-1,3-propanediol,

melting point=112°-113° C.

EXAMPLE 125 2-Acetamido-1,3-diacetoxy-2-(4-nonylphenylmethyl)propane,melting point=85°-89° C. EXAMPLE 126 2-Amino-2-3-(4-heptylphenyl)propyl!-1,3-propanediol 1/2 hydrate, meltingpoint=78°-80° C. EXAMPLE 127 2-Acetamido-1,3-diacetoxy-2-3-(4-heptylphenyl)propyl!propane, melting point=62°-64° C. EXAMPLE 1282-Amino-2- 3-(4-undecylphenyl)propyl!-1,3-propanediol, meltingpoint=89°-91° C. EXAMPLE 129 2-Acetamido-1,3-diacetoxy-2-3-(4-undecylphenyl)propyl!propane, melting point=64°-67° C. EXAMPLE 1302-Amino-2- 4-(4-octylphenyl)butyl!-1,3-propanediol hydrochloride,melting point=108°-110° C. EXAMPLE 131 2-Acetamido-1,3-diacetoxy-2-4-(4-octylphenyl)butyl!propane, melting point=64°-67° C. EXAMPLE 1322-Amino-2- 6-(4-butylphenyl)hexyl!-1,3-propanediol, meltingpoint=70°-71° C. EXAMPLE 133 2-Acetamido-1,3-diacetoxy-2-6-(4-butylphenyl)hexyl!propane,

IR; 3300, 2930, 2858, 1748, 1660 cm⁻¹

EXAMPLE 134 2-Amino-2- 8-(4-ethylphenyl)octyl!-1,3-propanediolhydrochloride 1 hydrate, melting point=47°-48° C. EXAMPLE 1352-Acetamido-1,3-diacetoxy-2- 8-(4-ethylphenyl)octyl!propane, meltingpoint=58°-60° C. EXAMPLE 1362-Amino-2-(4-octyloxyphenylmethyl)-1,3-propanediol, meltingpoint=119°-120° C. EXAMPLE 1372-Acetamido-1,3-diacetoxy-2-(4-octyloxyphenylmethyl)propane, meltingpoint=77°-78° C. EXAMPLE 1382-Amino-2-(4-decyloxyphenylmethyl)-1,3-propanediol hydrochloride,melting point=100°-102° C. EXAMPLE 1392-Acetamido-1,3-diacetoxy-2-(4-decyloxyphenylmethyl)propane, meltingpoint=74°-77° C. EXAMPLE 140 2-Amino-2-2-(4-pentyloxyphenyl)ethyl!-1,3-propanediol hydrochloride,

melting point=134°-137° C.

EXAMPLE 141 2-Acetamido-1,3-diacetoxy-2-2-(4-pentyloxyphenyl)ethyl!propane, melting point=93°-95° C. EXAMPLE 1422-Amino-2- 3-(4-hexyloxyphenyl)propyl!-1,3-propanediol, meltingpoint=70°-71° C. EXAMPLE 143 2-Acetamido-1,3-diacetoxy-2-3-(4-hexyloxyphenyl)propyl!propane, melting point=70°-72.5° C. EXAMPLE144 2-Amino-2- 3-(4-heptyloxyphenyl)propyl!-1,3-propanediolhydrochloride 1/6 hydrate,

melting point=111°-113° C.

EXAMPLE 145 2-Acetamido-2- 3-(4-heptyloxyphenyl)propyl!-1,3-propanediol,melting point=93°-95° C. EXAMPLE 146 2-Amino-2-3-(4-octyloxyphenyl)propyl!-1,3-propanediol, melting point=73°-75° C.EXAMPLE 147 2-Acetamido-1,3-diacetoxy-2-3-(4-octyloxyphenyl)propyl!propane, melting point=66°-69° C. EXAMPLE 1482-Amino-2- 4-(4-decyloxyphenyl)propyl!-1,3-propanediol, meltingpoint=60°-62° C. EXAMPLE 149 2-Acetamido-1,3-diacetoxy-2-4-(4-decyloxyphenyl)propyl!propane, melting point=66°-67° C. EXAMPLE 1502-Amino-2- 3-(3-heptyloxyphenyl)propyl!-1,3-propanediol hydrochloride,

melting point=102°-103° C.

EXAMPLE 151 2-Acetamido-2- 3-(3-heptyloxyphenyl)propyl!-1,3-propanediol,

IR; 3305, 2932, 1652, 1376 cm⁻¹

EXAMPLE 152 2-Amino-2- 4-(4-pentyloxyphenyl)butyl!-1,3-propanediol,melting point=79°-80° C. EXAMPLE 153 2-Acetamido-1,3-diacetoxy-2-4-(4-pentyloxyphenyl)butyl!propane, melting point=83°-84° C. EXAMPLE 1542-Amino-2- 4-(4-hexyloxyphenyl)butyl!-1,3-propanediol hydrochloride,

melting point=99°-100° C.

EXAMPLE 155 2-Acetamido-1,3-diacetoxy-2-4-(4-hexyloxyphenyl)butyl!propane, melting point=83°-87° C. EXAMPLE 1562-Amino-2- 5-(4-butoxyphenyl)pentyl!-1,3-propanediol hydrochloride,melting point=79°-80° C. EXAMPLE 157 2-Acetamido-1,3-diacetoxy-2-5-(4-butoxyphenyl)pentyl!propane, melting point=71°-73° C. EXAMPLE 1582-Amino-2- 8-(4-methoxyphenyl)octyl!-1,3-propanediol, meltingpoint=69°-70° C. EXAMPLE 159 2-Acetamido-1,3-diacetoxy-2-8-(4-methoxyphenyl)octyl!propane,

IR; 3301, 1745, 1662, 1246 cm⁻¹

EXAMPLE 160 2-Amino-2- 4-(4-chlorophenyl)butyl!-1,3-propanediol, meltingpoint=75°-79° C. EXAMPLE 161 2-Acetamido-1,3-diacetoxy-2-4-(4-chlorophenyl)butyl!propane, melting point=82°-84° C. EXAMPLE 1622-Amino-2- 3-(4-decanoylaminophenyl)propyl!-1,3-propanediol 1/4 hydrate,melting point=112°-113° C. EXAMPLE 163 2-t-Butoxycarbonylamino-2-3-(4-decanoylaminophenyl)propyl!propane,

melting point=93°-94° C.

EXAMPLE 164 2-Amino-2- 3-(4-decylaminophenyl)propyl!-1,3-propanediol 1/2hydrate, melting point=100°-102° C. EXAMPLE 165 2-Amino-2-{7-2-(4-hexylphenyl)-1,3-dioxolan-2-yl!heptyl}-1,3-propanediol 1/2 hydratehydrochloride,

IR; 3346, 1610, 1510, 1047 cm⁻¹

EXAMPLE 166 2-Acetamido-1,3-diacetoxy-2-{7-2-(4-hexylphenyl)-1,3-dioxolan-2-yl!heptyl}propane,

IR; 3308, 1745, 1660, 1238, 1043 cm⁻¹

EXAMPLE 167 2-Amino-2- 7-(4-hexylbenzoyl)heptyl!-1,3-propanediolhydrochloride,

melting point=114°-115° C.

EXAMPLE 168 2-Amino-2- 8-(4-hexylphenyl)octyl!-1,3-propanediol, meltingpoint=71°-73° C. EXAMPLE 169 2-Acetamido-1,3-diacetoxy-2-8-(4-hexylphenyl)octyl!propane,

IR; 3306, 1745, 1660, 1240 cm⁻¹

EXAMPLE 170 2-Amino-2-{3-4-(2-decyl-1,3-dioxolan-2-yl)phenyl!propyl}-1,3-propanediol 2/3 hydrate,

IR; 3346, 1037 cm⁻¹

EXAMPLE 171 2-Acetamido-1,3-diacetoxy-2-{3-4-(2-decyl-1,3-dioxolan-2-yl)phenyl!propyl)propane,

melting point=45°-47° C.

EXAMPLE 172 2-Acetamido-1,3-diacetoxy-2-{3-4-(2-hexyl-1,3-dioxolan-2-yl)phenyl!propyl)propane 3/5 hydrate,

melting point=48°-50° C.

EXAMPLE 173 2-Amino-2- 3-(4-decanoylphenyl)propyl!-1,3-propanediolhydrochloride,

melting point=126°-127° C.

EXAMPLE 174 2-Amino-2- 3-(4-heptanoylphenyl)propyl!-1,3-propanediolhydrochloride,

melting point=129°-130° C.

EXAMPLE 175 2-Amino-2-{2-4-(5-phenylpentyloxymethyl)phenyl!ethyl!-1,3-propanediol hydrochloride3/2 hydrate, melting point=105°-108° C. EXAMPLE 1762-Acetamido-1,3-diacetoxy-2-{2-4-(5-phenylpentyloxymethyl)phenyl!ethyl}propane,

IR; 3308, 1738, 1651, 1226 cm⁻¹

EXAMPLE 177 2-Amino-2- 6-(4-hexyloxyphenyloxy)hexyl!-1,3-propanediolhydrochloride 5/4 hydrate,

melting point=90°-95° C.

EXAMPLE 178 2-Acetamido-2-6-(4-hexyloxyphenyloxy)hexyl!-1,3-propanediol, melting point=81°-83° C.EXAMPLE 179 2-Amino-2- 6-(2-phenyloxyethyloxy)hexyl!-1,3-propanediol,melting point=90°-93° C. EXAMPLE 180 2-Acetamido-1,3-diacetoxy-2-6-(2-phenyloxyethyloxy)hexyl!propane,

IR; 2935, 2864, 1744, 1660, 1245 cm⁻¹

EXAMPLE 181 2-Acetamido-2-(12-phenyloxydodecyl)-1,3-propanediol, meltingpoint=76°-77° C. EXAMPLE 1822-Amino-2-(12-phenyloxydodecyl)-1,3-propanediol hydrochloride EXAMPLE183 2-(N,N-Dimethylamino)-2- 2-(4-octylphenyl)ethyl!-1,3-propanediolEXAMPLE 184 2-Amino-2- 2-(4-hexyloxyphenyl)ethyl!-1,3-propanediolEXAMPLE 185 2-Acetamido-1,3-diacetoxy-2-2-(4-hexyloxyphenyl)ethyl!propane EXAMPLE 186 2-Amino-2-{2-4-(8-fluorooctyl)phenyl!ethyl}-1,3-propanediol EXAMPLE 1872-Acetamido-1,3-diacetoxy-2-{2- 4-(8-fluorooctyl)phenyl!ethyl}propaneEXAMPLE 188 2-Amino-2-{2-4-(7-fluoroheptyloxy)phenyl!ethyl}-1,3-propanediol white amorphous-likesolid

Rf value=0.09 (chloroform:methanol=9:1)

¹ H-NMR (DMSO-d₆) δ; 1.26°-1.64 (14H, m), 3.50 (4H, s), 3.90 (2H, t,J=6.3 Hz), 4.42 (2H, td, J=47.4 Hz, 6.3 Hz), 5.48 (2H, br.s), 6.83 (2H,d, J=8.8 Hz), 7.09 (2H, d, J=8.8 Hz), 7.86 (3H, br.s)

IR(KBr) 3391, 1612, 1581, 1249, 831 cm⁻¹

elemental analysis: calculated C 56.61, H 8.71, N 3.67 found C 57.00, H8.58, N 3.69

EXAMPLE 189 2-Acetamido-1,3-diacetoxy-2-{2-4-(7-fluoroheptyloxy)phenyl!ethyl}propane, colorless liquid

Rf value=0.70 (ethyl acetate)

IR(neat) 3310, 1738, 1651, 1614, 1514, 1244, 815 cm⁻¹

EXAMPLE 190 2-Amino-2-{2-4-(1,1-difluorooctyl)phenyl!ethyl}-1,3-propanediol EXAMPLE 1912-Acetamido-1,3-diacetoxy-2-{2-4-(1,1-difluorooctyl)phenyl!ethyl}propane EXAMPLE 192 2-Amino-2-{2-4-(1,1-difluoroheptyloxy)phenyl!ethyl}-1,3-propanediol EXAMPLE 1932-Acetamido-1,3-diacetoxy-2-{2-4-(1,1-difluoroheptyloxy)phenyl!ethyl!propane EXAMPLE 194 2-Amino-2-{2-4-(4-methylpentyl)phenyl!ethyl}-1,3-propanediol EXAMPLE 1952-Acetamido-1,3-diacetoxy-2-{2- 4-(4-methylpentyl)phenyl!ethyl}propaneEXAMPLE 196 2-Amino-2- 2-(4-fluorophenyl)ethyl!-1,3-propanediolhydrochloride, melting point=169°-170° C. EXAMPLE 197 2-Acetamido-2-2-(4-fluorophenyl)ethyl!-1,3-propanediol, melting point=63°-65° C.EXAMPLE 198 2-Acetamido-1,3-diacetoxy-2- 2-(4-fluorophenyl)ethyl!propaneEXAMPLE 199 2-Amino-2- 2-(3-fluoro-4-octylphenyl)ethyl!-1,3-propanediolEXAMPLE 200 2-Acetamido-1,3-diacetoxy-2-2-(3-fluoro-4-octylphenyl)ethyl!propane EXAMPLE 201 2-Amino-2-2-(2-ethyl-4-octylphenyl)ethyl!-1,3-propanediol EXAMPLE 2022-Acetamido-1,3-diacetoxy-2- 2-(2-ethyl-4-octylphenyl)ethyl!propaneEXAMPLE 203 2-Amino-2- 2-(3-methyl-4-octylphenyl)ethyl!-1,3-propanediolEXAMPLE 204 2-Acetamido-1,3-diacetoxy-2-2-(3-methyl-4-octylphenyl)ethyl!propane EXAMPLE 205 2-Amino-2-2-(4-heptyloxy-3-methoxyphenyl)ethyl!-1,3-propanediol 1/2 hydratehydrochloride,

melting point=126°-129° C.

¹ H-NMR (CDCl₃) δ: 0.80 (3H, t, J=6 Hz), 1.22°-1.36 (8H, m), 1.70-1.76(2H, m), 1.83-1.91 (2H, m), 2.50-2.54 (2H, m), 3.30 (3H, s), 3.77 (4H,s), 3.89 (2H, t, J=8 Hz), 6.63-6.72 (3H, m)

IR ν 3179, 2931, 1617, 1518, 1240, 1036 cm⁻¹

EXAMPLE 206 2-Acetamido-1,3-diacetoxy-2-2-(4-heptyloxy-3-methoxyphenyl)ethyl!propane,

melting point=138°-139° C.

¹ H-NMR (CDCl₃ ) δ: 0.88 (3H, t, J=6 Hz), 1.30-1.56 (10H, m), 1.96 (3H,s), 2.09 (6H, s), 2.18-2.22 (2H, m), 2.53-2.57 (2H, m), 3.86 (3H, s),3.97 (2H, t, J=6 Hz), 4.35 (4H, s), 5.65 (1H, s), 6.70-6.80 (3H, m)

IR ν 3291,.2930, 1738, 1258 cm⁻¹

elemental analysis: calculated C 64.49, H 8.44, N 3.01 found C 64.32, H8.33, N 3.03

EXAMPLE 207 2-Amino-2-2-(4-heptyloxy-3-methylphenyl)ethyl!-1,3-propanediol EXAMPLE 2082-Acetamido-1,3-diacetoxy-2- 2-(4-heptyloxy-3-methylphenyl)ethyl!propaneEXAMPLE 209 2-Amino-2- 2-(4-phenylmethyloxyphenyl)ethyl!-1,3-propanediol1/5 hydrate hydrochloride

melting point=207°-210° C.

¹ H-NMR (CDCl₃) δ: 1.90-1.95 (2H, m), 2.59-2.63 (2H, m), 3.71 (4H, q,J=12 Hz), 5.04 (2H, s), 6.91 (2H, d, J=8 Hz), 7.13 (2H, d, J=8 Hz),7.37-7.44 (5H, m)

IR ν 3422, 1617, 1508, 1245 cm⁻¹

EXAMPLE 210 2-Acetamido-1,3-diacetoxy-2-2-(4-phenylmethyloxyphenyl)ethyl!propane, melting point=150°-153° C.

¹ H-NMR (CDCl₃)δ: 1.95 (3H, s), 2.09 (6H, s), 2.15-2.20 (2H, m),2.53-2.58 (2H, m), 4.34 (4H, s), 5.04 (2H, s), 5.64 (1H, s), 6.90 (2H,d, J=8 Hz), 7.10 (2H, d, J=8 Hz), 7.36-7.43 (5H, m)

IR ν 3318, 1763, 1736, 1654, 1250 cm⁻¹

elemental analysis: calculated C 67.43, H 6.84, N 3.28 found C 67.47, H6.96, N 3.19

EXAMPLE 211 2-Amino-2- 2-(4-hydroxyphenyl)ethyl!-1,3-propanediol,melting point: 180°-185° C.

¹ H-NMR (CDCl₃) δ: 1.61-1.66 (2H, m), 2.52-2.57 (2H, m), 3.57 (4H, s),6.74 (2H, d, J=8 Hz), 7.03 (2H, d, J=8 Hz)

IR ν 3355, 2923, 1602, 1474, 1232 cm⁻¹

elemental analysis: calculated C 62.54, H 8.11, N 6.63 found C 62.45, H8.07, N 6.68

EXAMPLE 212 2-Acetamido-1,3-diacetoxy-2-2-(4-hydroxyphenyl)ethyl!propane, melting point=100°-105° C.

¹ H-NMR (CDCl₃) δ: 1.98 (3H, s), 2.10 (6H, s), 2.17-2.22 (2H, m),2.52-2.56 (2H, m), 4.34 (4H, s), 5.73 (1H, s), 6.76 (2H, d, J=9 Hz),7.03 (2H, d, J=9 Hz)

IR ν 3590, 1741, 1577, 1243 cm⁻¹

EXAMPLE 213 2-Amino-2-(9-phenyloxynonyl)-1,3-propanediol hydrochloride,melting point=103°-104° C.

elemental analysis: calculated C 62.50, H 9.32, N 4.05 found C 62.21, H9.39, N 3.95

EXAMPLE 214 2-Acetamido-2-(9-phenyloxynonyl)-1,3-propanediol

melting point=71°-73° C.

elemental analysis: calculated C 68.34, H 9.46, N 3.99 found C 68.34, H9.44, N 3.01

EXAMPLE 215 2-Acetamido-1,3-diacetoxy-2-(9-phenyloxynonyl)propaneEXAMPLE 216 2-Amino-2-(12-fluorododecyl)-1,3-propanediol 1/10 hydratehydrochloride,

melting point=87°-89° C.

EXAMPLE 217 2-Acetamido-1,3-diacetoxy-2-(12-fluorododecyl)propane,melting point=57°-59° C. EXAMPLE 2182-Amino-2-(13-fluorotridecyl)-1,3-propanediol EXAMPLE 2192-Acetamido-1,3-diacetoxy-2-(13-fluorotridecyl)propane EXAMPLE 2202-Amino-2-{2- 4-(N-decyl-N-methylamino)phenyl!ethyl)-1,3-propanediolEXAMPLE 221 2-Acetamido-1,3-diacetoxy-2-{2-4-(N-decyl-N-methylamino)phenyl!ethyl}propane EXAMPLE 222 2-Amino-2-2-(4-heptylthiophenyl)ethyl!-1,3-propanediol EXAMPLE 2232-Acetamido-1,3-diacetoxy-2- 2-(4-heptylthiophenyl)ethyl!propane EXAMPLE224 2-Amino-2- 2-(4-heptylphenyl)ethyl!-1,3-propanediol EXAMPLE 2252-Acetamido-1,3-diacetoxy-2- 2-(4-heptylphenyl)ethyl!propane EXAMPLE 2262-Amino-2- 2-(4-heptylphenyl)-2-oxoethyl!-1,3-propanediol EXAMPLE 2272-Acetamido-1,3-diacetoxy-2- 2-(4-heptylphenyl)-2-oxoethyl!propaneEXAMPLE 228 2-Amino-2-2-(4-heptylphenyl)-2-hydroxyethyl!-1,3-propanediol EXAMPLE 2292-Acetamido-1,3-diacetoxy-2- 2-(4-heptylphenyl)-2-hydroxyethyl!propaneEXAMPLE 230 2-Amino-2-{2-2-(4-heptylphenyl)-1,3-dioxolan-2-yl!ethyl}-1,3-propanediol EXAMPLE 2312-Acetamido-1,3-diacetoxy-2-{2-2-(4-heptylphenyl)-1,3-dioxolan-2-yl!ethyl}propane EXAMPLE 2322-Amino-2- 2-(4-octylphenyl)-2-oxoethyl!-1,3-propanediol EXAMPLE 2332-Acetamido-1,3-diacetoxy-2- 2-(4-octylphenyl)-2-oxoethyl!propaneEXAMPLE 234 2-Amino-2- 2-(4-octylphenyl)-2-hydroxyethyl!-1,3-propanediolEXAMPLE 235 2-Acetamido-1,3-diacetoxy-2-2-(4-octylphenyl)-2-hydroxyethyl!propane EXAMPLE 236 2-Amino-2-{2-2-(4-octylphenyl)-1,3-dioxolan-2-yl!ethyl}-1,3-propanediol EXAMPLE 2372-Acetamido-1,3-diacetoxy-2-{2-2-(4-octylphenyl)-1,3-dioxolan-2-yl!ethyl}propane EXAMPLE 2612-Amino-2-(8-hydroxytetradecyl)-1,3-propanediol hydrochloride

(1) 2-Acetamido-3-acetoxy-2-acetoxymethyl-14-oxoicosa-6-enoicacid-δ-lactone

Acetic anhydride (200 ml) and pyridine (20 ml) were added to2-amino-3,4-dihydroxy-2-dihydroxymethyl-14-oxoicosa-6-enoic acid (20 g)and the mixture was stirred at room temperature overnight. The reactionmixture was poured into ice water and extracted with ethyl acetate. Theethyl acetate layer was washed with 1N hydrochloric acid, a saturatedaqueous sodium hydrogencarbonate solution and saturated brine in order.The resultant mixture was dried over magnesium sulfate and the solventwas distilled away to give the subject compound (22.9 g).

(2) 14-Hydroxy-2-acetamido-3-acetoxy-2-acetoxymethyl-14-oxoicosa-6-enoicacid-δ-lactone

Deionized water (150 ml) was added to a solution of the above-mentionedcompound (12.8 g) in dioxane. The mixture was stirred in an ice bath forabout 30 minutes while bubbling carbon dioxide to saturation, thereby tomake the solution weak acidic. Sodium borohydride (2.41 g) was addedthereto and the mixture was stirred for 1 hour. The reaction mixture wasacidified with 1N hydrochloric acid and made weak acidic with 1N sodiumhydroxide. The resultant mixture was concentrated and extracted withethyl acetate. The ethyl acetate layer was washed with a saturatedsodium hydrogencarbonate solution and saturated brine in order and driedover magnesium sulfate. The solvent was distilled away and the residueobtained was purified by silica gel column chromatography (eluent;chloroform: methanol=50:1) to give the subject compound (7.49 g).

IR: 3440, 2920, 2850, 1750, 1680 cm⁻¹

(3)14-t-Butyldimethylsilyloxy-2-acetamido-3-acetoxy-2-acetoxymethyl-14-oxoicosa-6-enoicacid-δ-lactone

Imidazole (4.97 g) and t-butyldimethylsilyl chloride (5.50 g) were addedto a solution of the compound (7.49 g) as mentioned above inN,N-dimethylformamide (75 ml) and the mixture was stirred at 60° C. for1 hour. Deionized water was added to the reaction mixture underice-cooling and the mixture was stirred for 30 minutes and then at roomtemperature for 30 minutes. Deionized water was added thereto and themixture was extracted with diethyl ether. The diethyl ether layer wasconcentrated and dried over magnesium sulfate. The solvent was distilledaway and the residue obtained was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:2) to give the subjectcompound (8.50 g).

IR: 3440, 2920, 2850, 1750, 1680, 830 cm⁻¹

(4)5,6-Dihydroxy-14-t-butyldimethylsilyloxy-2-acetamido-3-acetoxy-2-acetoxymethyl-14-oxoicosa-6-enoicacid-δ-lactone

N-Methylmorpholine-N-oxide (3.19 g) and a 1% aqueous osmium tetraoxidesolution (34.5 ml) were added to a solution of the compound (8.50 g) asmentioned above in acetone (207 ml) and the mixture was stirred at roomtemperature for 2 hours. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed with asaturated sodium sulfite solution, 1N hydrochloric acid, a saturatedsodium hydrogencarbonate solution and saturated brine in order and driedover magnesium sulfate. The solvent was distilled away to give thesubject compound (8.05 g).

IR: 3440, 2920, 2850, 1750, 1680, 830 cm⁻¹

(5) 8-t-Butyldimethylsilyloxytetradecanal

A 0.2N aqueous sodium periodate solution (183 ml) was added to asolution of the compound (8.05 g) as mentioned above in dioxane (610 ml)and the mixture was stirred at room temperature for 2 hours. Thereaction mixture was concentrated and extracted with hexane. The hexanelayer was dried over magnesium sulfate and the solvent was distilledaway to give the subject compound (4.1 g, yield 98.4%).

IR: 2920, 2850, 1720, 830 cm⁻¹

(6) 8-t-Butyldimethylsilyloxytetradecanol

Deionized water (40 ml) was added to a solution of the compound (4.1 g)as mentioned above in dioxane (120 ml) and sodium borohydride (1.15 g)was added thereto under ice-cooling. The mixture was stirred at roomtemperature for 30 minutes. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed with 1Nhydrochloric acid, a saturated sodium hydrogencarbonate solution andsaturated-brine in order, and dried over magnesium sulfate. The solventwas distilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:10) to give thesubject compound (3.74 g).

IR: 2920, 2850, 1710, 830 cm⁻¹

(7) 1-Iodo-8-t-butyldimethylsilyloxytetradecane

Imidazole (1.85 g), triphenylphosphine (7.14 g) and iodine (5.53 g) wereadded to a solution of the compound (3.74 g) as mentioned above inbenzene (200 ml) and the mixture was stirred at room temperature for 30minutes. The reaction mixture was extracted with ethyl acetate andwashed with a saturated sodium sulfite solution and saturated brine inorder. The ethyl acetate layer was dried over magnesium sulfate and thesolvent was distilled away. The residue obtained was purified by silicagel column chromatography (eluent; hexane) to give the subject compound(4.42 g).

IR: 2920, 2850, 830 cm⁻¹

(8) Diethyl 2-acetamido-2-(8-t-butyldimethylsilyloxytetradecyl)malonate

Diethyl acetamidomalonate (2.54 g) and sodium ethoxide (0.80 g) wereadded to a solution of the compound (4.42 g) as mentioned above indehydrated ethanol (200ml) and the mixture was refluxed under heating ina stream of nitrogen overnight. The reaction mixture was concentratedand the residue obtained was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:5→1:3) to give thesubject compound (2.81 g).

¹ H-NMR (CDCl₃) δ: 0.03 (6H, s), 0.84 (12H, m), 1.23 (18H, m), 1.23 (6H,t, J=7.0 Hz), 1.35 (4H, m), 2.01 (3H, s), 2.28 (2H, m), 3.57 (1H, q,J=6.0 Hz), 4.215 (4H, q, J=7 Hz), 6.74 (1H, s)

IR: 3440, 2920, 2850, 1740, 1680, 830 cm⁻¹

(9)2-Acetamido-1,3-diacetoxy-2-(8-t-butyldimethylsilyloxytetradecyl)propane

Sodium borohydride (1.77 g) was added to a solution of the compound(3.38 g) as mentioned above in methanol (13 ml) and the mixture wasallowed to stand at room temperature for 1 hour. The reaction mixturewas extracted with ethyl acetate and washed with 1N hydrochloric acid, asaturated sodium hydrogencarbonate solution and saturated brine inorder. The ethyl acetate layer was dried over magnesium sulfate and thesolvent was distilled away. Acetic anhydride (19.6 ml) and pyridine(1.96 ml) were added to the residue obtained and the mixture was stirredat room temperature overnight. The reaction mixture was poured into icewater and extracted with ethyl acetate. The ethyl acetate layer waswashed with 1N hydrochloric acid, a saturated sodium hydrogencarbonatesolution and saturated brine in order and dried over magnesium sulfate.The solvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:2) togive the subject compound (2.04 g).

¹ H-NMR (CDCl₃) δ: 0.009 (6H, s), 0.86 (3H, t), 0.86 (9H, s), 1.24 (18H,m), 1.36 (4H, m), 1.82 (2H, m), 1.94 (3H, s), 2.06 (6H, s), 3.58 (1H, q,J=8 Hz), 4.26 (2H, d, J=11.2 Hz), 4.29 (2H, d, J=11.3 Hz), 5.59 (1H, s)

IR: 3440, 2920, 2850, 1740, 1680, 830 cm⁻¹

(10) 2-Acetamido-1,3-diacetoxy-2-(8-hydroxytetradecyl)propane

A solution of the compound (2.04 g) as mentioned above in 0.01Nhydrochloric acid-methanol (37.6 ml) was allowed to stand at roomtemperature for 3 hours. Deionized water was added thereto and themixture was extracted with ethyl acetate. The ethyl acetate layer waswashed with a saturated sodium hydrogencarbonate solution and asaturated sodium chloride solution in order and dried over magnesiumsulfate. The solvent was distilled away and the residue obtained waspurified by silica gel column chromatography (eluent; ethylacetate:hexane=1:1) to give the subject compound (1.15 g).

melting point=82°-84° C.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=6.9 Hz), 1.26 (18H, m), 1.40 (4H, m),1.82 (2H, m), 1.93 (3H, s), 2.05 (6H, s), 3.55 (1H, m), 4.25 (2H, d,J=11.2 Hz), 4.28 (2H, d, J=11.7 Hz), 5.59 (1H, s)

IR: 3440, 2920, 2850, 1720, 1680 cm⁻¹

(11) 2-Amino-2-(8-hydroxytetradecyl)-1,3-propanediol hydrochloride

1N Sodium hydroxide was added to a solution of the compound (300 mg) asmentioned above in methanol (12.6 ml) and the mixture was refluxed underheating in a stream of nitrogen for 6 hours. The reaction mixture wasconcentrated and extracted with ethyl acetate. The ethyl acetate layerwas washed with saturated brine and dried over magnesium sulfate. Thesolvent was distilled away. 1N Hydrochloric acid-methanol (1.4 ml) wasadded to the residue obtained and the mixture was concentrated to givethe subject compound (230 mg).

melting point=106°-108° C.

¹ H-NMR (CDCl₃) δ: 0.84 (3H, t, J=6.8 Hz), 1.22 (22H, m), 1.48 (2H, d,J=10.3 Hz), 3.40 (2H, d, J=10.3 Hz), 3.44 (2H, d, J=12.2 Hz), 4.21 (1H,m), 5.28 (2H, br.s), 1.14 (3H, br.s)

IR: 3350, 2900, 2850 cm⁻¹

EXAMPLE 262 2-Amino-2-(8-oxotetradecyl)-1,3-propanediol hydrochloride

(1) 2-Acetamido-1,3-diacetoxy-2-(8-oxotetradecyl)propane

Pyridinium chlorochromate (301.5 mg) was added to a solution of2-acetamido-1,3-diacetoxy-2-(8-hydroxytetradecyl)propane (300 mg) indichloromethane (19 ml) and the mixture was stirred at room temperaturefor 2 hours in a stream of nitrogen. Ether (38 ml) and magnesium sulfate(appropriate amount) were added thereto and the mixture Was stirred for10 minutes. The reaction mixture was suction-filtered and the filtratewas concentrated. The concentrate was extracted with ethyl acetate andthe ethyl acetate layer was washed with 1N hydrochloric acid, asaturated sodium hydrogencarbonate solution and saturated brine inorder. The resultant mixture was dried over magnesium sulfate. Thesolvent was distilled away to give the subject compound (290 mg).

melting point=88°-89° C.

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=7.1 Hz), 1.27 (14H, m), 1.55 (4H, m),1.84 (2H, dd, J=8.8, 15.6 Hz), 1.97 (3H, s) 2.08 (6H, s), 2.38 (4H, t,J=7.4 Hz), 4.28 (2H, d, J=11.3 Hz), 4.31 (2H, d, J=11.2 Hz), 5.63 (1H,s)

IR: 2920, 2850, 1740-1680 cm⁻¹

(2) 2-Amino-2-(8-oxotetradecyl)-1,3-propanediol hydrochloride

1N Sodium hydroxide (4.1 ml) was added to a solution of the compound(290 mg) as mentioned above in methanol (12.2 ml) and the mixture wasrefluxed under heating in a nitrogen flow for 6 hours. The reactionmixture was concentrated and extracted with ethyl acetate. The ethylacetate layer was washed with saturated brine and dried over magnesiumsulfate. The solvent was distilled away and 1N hydrochloricacid-methanol (1.2 ml) was added to the residue obtained. The mixturewas concentrated and the residue obtained was recrystallized from ethylacetate to give the subject compound (176 mg).

melting point=121°-122° C.

¹ H-NMR (CDCl₃) δ: 0.614 (3H, t, J=6.3 Hz), 1.03 (18H, m), 1.28 (4H, m),1.41 (2H, m), 2.12 (4H, t, J=7.3 Hz| , 3.38 (2H, d, J=12.2 Hz), 3.48(2H, d, J=12.2 Hz), 4.71 (2H, br.s), 7.65 (3H, br.s)

IR: 3420, 3340, 3030, 2920, 2850, 1700 cm⁻¹

EXAMPLE 263 2-Amino-2-(2-N-dodecylaminoethyl)-1,3-propanediolhydrochloride

(1) Diethyl aminomalonate hydrochloride (10 g) was dissolved in 100 mlof N,N-dimethylformamide, and 6.3 g of triethylamine and 12.1 g ofdi-t-butyldicarbonate Were added thereto. The mixture was stirred at 60°C. for 1 hour. Water was added to the reaction mixture under ice-coolingand the mixture was stirred at room temperature. The reaction mixturewas extracted with ether, dried and concentrated. The resultant mixturewas purified by silica gel column chromatography using hexane-ethylacetate (10:1→5:1) as an eluent to give 13 g of colorless, oily diethylN-t-butoxycarbonylaminomalonate.

IR ν_(max) (CHCl₃): 3450, 2970, 1740(sh), 1710, 1490, 1375, 1340, 1160,1060, 1020, 860 cm⁻¹

(2) Diethyl N-t-butoxycarbonylaminomalonate (5 g) was dissolved in 100ml of dehydrated ethanol, and 1.53 g of sodium ethoxide and 2.7 g ofaryl bromide were added thereto. The mixture was refluxed under anitrogen atmosphere for 12 hours. The reaction mixture was concentratedand purified by silica gel column chromatography using hexane-ethylacetate (20:1→10:1→8:1) to give 4.8 g of colorless, oily diethyl2-aryl-N-t-butoxycarbonylaminomalonate.

IR ν_(max) (CHCl₃): 3450, 2980, 2860, 1740(sh), 1710, 1480, 1400, 1370,1310, 1160, 1080, 1060, 1020, 915, 860 cm⁻¹

(3) Diethyl 2-aryl-N-t-butoxycarbonylaminomalonate (4.8 g) was dissolvedin 30 ml of methanol and 4.34 g of sodium borohydride was added thereto.The mixture was allowed to stand at room temperature for 2 hours. Ethylacetate was added to the reaction mixture and the mixture was washedwith a 1N aqueous hydrochloric acid solution, a saturated aqueous sodiumhydrogencarbonate solution and a saturated aqueous sodium chloridesolution. The resultant mixture was dried and concentrated. The residuewas dissolved in 32 ml of N,N-dimethylformamide, and 5.72 g of imidazoleand 6.33 g of t-butyldimethylsilyl chloride were added thereto. Themixture was stirred at 60° C. for 1 hour.

Water was added to the reaction mixture under ice-cooling and themixture was stirred at room temperature. The resultant mixture wasextracted with ether, dried and concentrated. The concentrate waspurified by silica gel column chromatography using hexane-ethyl acetate(10:1) as an eluent to give 3.8 g of colorless, oily2-aryl-2-(N-t-butoxycarbonylamino)-1,3-propanediolbis-t-butyldimethylsilyl ether.

Rf value=0.7 (hexane-ethyl acetate=10:1)

(4) 2-Aryl-2-(N-t-butoxycarbonylamino)-1,3-propanediolbis-t-butyldimethylsilyl ether (3.8 g) was dissolved in 300 ml ofacetone, and 2.45 g of N-methylmorpholine-N-oxide and 43 ml of a 1%aqueous osmium tetraoxide solution were added thereto. The mixture wasstirred at room temperature for 4 hours. The reaction mixture wasconcentrated and ethyl acetate was added thereto. The mixture was washedwith a saturated aqueous sodium sulfite solution, a 1N aqueoushydrochloric acid solution, a saturated aqueous sodium hydrogencarbonatesolution and a saturated aqueous sodium chloride solution. Afterdehydration, the resultant mixture was concentrated to give 4.3 g ofcolorless, oily2-(2,3-dihydroxypropyl)-2-(N-t-butoxycarbonylamino)-1,3-propanediolbis-t-butyldimethylsilyl ether.

IR ν_(max) (CHCl₃): 3450(br), 2940, 2850, 1710, 1500, 1470, 1400, 1370,1260, 1160, 1080(br), 840 cm⁻¹

(5) 2-(2,3-Dihydroxypropyl)-2-(N-t-butoxycarbonylamino)-1,3-propanediolbis-t-butyldimethylsilyl ether (4.3 g) was dissolved in 600 ml of1,4-dioxane and a solution of 3.8 g of meta-sodium periodate in 90 ml ofwater was added thereto. The mixture was stirred at room temperature for3 hours. The reaction mixture was concentrated and hexane was addedthereto. After washing with water, the resultant mixture was dehydratedand concentrated to give 3.76 g of colorless, oily2-(N-t-butoxycarbonylamino)-2-(2-formylethyl)-1,3-propanediolbis-t-butyldimethylsilyl ether.

Rf value=0.7 (hexane-ethyl acetate=5:1)

(6) 2-(N-t-Butoxycarbonylamino)-2-(2-formylethyl)-1,3-propanediolbis-t-butyldimethylsilyl ether (1.2 g) was dissolved in 20 ml ofmethanol and a solution of 2.89 g of dodecylamine in 5.2 ml ofconcentrated hydrochloric acid-methanol (1:11) and 245 mg of sodiumcyanoborohydride were added thereto. The mixture was stirred at roomtemperature overnight. The reaction mixture was concentrated and ethylacetate was added thereto. A 1N aqueous hydrochloric acid solution wasadded until the aqueous layer assumed acidity; a 1N aqueous sodiumhydroxide solution was added until the aqueous layer assumed weakacidity; and the solution was partitioned. The ethyl acetate layer waswashed with a saturated aqueous sodium chloride solution, dried andconcentrated. The. resultant mixture was purified by silica gel columnchromatography using hexane-ethyl acetate (3:1→2:1→1:1) as an eluent togive 956 mg of colorless, oily2-(2-N-dodecylaminoethyl)-2-(butoxycarbonylamino)-1,3-propanediolbis-t-butyldimethylsilyl ether.

IR ν_(max) (CHCl₃): 3450, 2920, 2850, 1710, 1500, 1460, 1400, 1370,1260, 1160, 1100(br), 840 cm⁻¹

¹ H-NMR (CDCl₃) δ: 5.31 (1H, s, NHBoc), 3.69 (2H, d, J=8 Hz, OCH_(2a)×2), 3.61 (2H, d, J=8 Hz, OCH₂ ×2), 2.66 (2H, t, J=8 Hz, H₂ C--N), 2.55(2H, t, J=8 Hz, N--CH₂), 1.85 (2H, t, J=8 Hz, --C--CH₂ ), 1.40 (9H, s,Boc.-t-Bu), 1.24 (20H, m, CH₂ ×10), 0.85 (21H, m, Si-tBu×2 and CH₂ CH₃), 0.03 (12H, s, Si--CH₃ ×4)

(7)2-(2-N-Dodecylaminoethyl)-2-(M-t-butoxycarbonylamino)-1,3-propanediolbis-t-butyldimethylsilyl ether (100 mg) was dissolved in 2 ml ofmethanol and 1.6 ml of concentrated hydrochloric acid-methanol (1:11)was added thereto. The mixture was warmed at 40° C. for 3 hours. Thereaction mixture was concentrated to give 58 mg of pale yellow, oily2-amino-2-(2-N-dodecylaminoethyl)-1,3-propanediol hydrochloride.

IR ν_(max) (KBr): 3350(br), 2920, 2850, 1600, 1460, 1060cm⁻¹

¹ H-NMR (DMSO-d₆) δ: 9.00 (2H, br.s, +NH₂ Cl⁻), 8.04 (3H, br.s, +NH₃Cl⁻), 5.51 (2H, s, OH×2), 3.47 (2H, s, OCH₂), 3.45 (2H, s, OCH₂), 2.99(2H, m, H₂ CN), 2.81 (2H, m, NCH₂), 1.96 (2H, m, --C--CH₂), 1.23 (20H,m, CH₂ ×10), 0.84 (3H, t, 6.8 Hz, CH₃)

EXAMPLE 264 2-Amino-2-(11-methoxycarbonylundecyl)-1,3-propanediolhydrochloride

2-Acetamido-1,3-diacetoxy-2-(12-hydroxydodecyl)propane (426 mg) wasdissolved in 2.7 ml of dry dimethylformamide and 1.345 g of pyridiniumdichromate was added thereto. The mixture was stirred at roomtemperature day and night under a nitrogen atmosphere. The reactionmixture was poured into water and extracted twice with ether. The etherlayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away under reduced pressure and 17 mlof methanol and 4.23 ml of a 1N aqueous sodium hydroxide solution wereadded to the residue. The mixture was refluxed under heating under anitrogen atmosphere for 6 hours. The reaction mixture was passed througha strongly acidic ion exchange resin, Amberlite IR-120B column, and theeluate was concentrated. The concentrate was dissolved in methanol andthe mixture was acidified with hydrochloric acid. The solvent wasdistilled away under reduced pressure to give 122 mg of the subjectcompound.

melting point=100.0°-104.0° C.

IR(cm⁻¹ ): 3370, 2920, 2850, 1740, 1500, 1470, 1170, 1080

NMR (DMSO) δ: 7.684 (3H, br.s), 5,275 (2H, br.s), 3.563 (3H, s), 3.441(1H, d, J=11.2 Hz), 3.430 (1H, d, J=11.2 Hz), 3.402 (1H, d, J=11.7 Hz),3.390 (1H, d, J=11.2 Hz), 2.272 (2H, t, J=7.3 Hz), 1.229 (2OH, s)

EXAMPLE 265 2-Amino-2-(11-carboxyundecyl)-1,3-propanediol hydrochloride

2N Hydrochloric acid (0.5 ml) was added to 10 mg of2-amino-2-(11-methoxycarbonylundecyl)-1,3-propanediol hydrochloride andthe mixture was heated at 90° C. for 1 hour. The solvent was distilledaway under reduced pressure to give 10 mg of the subject compound.

NMR (DMSO) δ: 11.992 (1H, br.s, COOH), 7.771 (3H, br.s, +NH₃), 5.292(2H, t, J=4.9 Hz, OH×2), 3.417 (4H, ddd, J=16.5, 11.7, 5.0 Hz, CH₂ O×2),2.168 (2H, t, J=7.4 Hz, CH₂ COO), 1.224 (2OH, 3, CH₂ ×10)

EXAMPLE 266 2-Acetamido-1,3-diacetoxy-2-(8-acetoxytetradecyl)propane

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=6.8 Hz), 1.24 (18H, m), 1.47 (4H, m),1.82 (2H, m), 1.94 (3H, s), 2.05-2.01 (9H, s), 4.25 (2H, d, J=11.7 Hz),4.29 (2H, d, J=11.7 Hz), 4.83 (1H, q, J=6.3 Hz), 5.62 (1H, s)

IR: 3400, 2920, 2850, 1720, 1680 cm⁻¹

EXAMPLE 267 2-Acetamido-1,3-diacetoxy-2-(3,7,11-trimethyldodecyl)propane

¹ H-NMR (CDCl₃) δ: 5.589 (1H, br.s), 4.293 (4H, dd, J=13.7, 12.3 Hz),2.073 (6H, s), 1.956 (3H, s), 1.857 (1H, qui, J=13.7 Hz), 1.844 (1H,qui, J=13.3 Hz), 1.513 (1H, septet, J=6.6 Hz), 1.345-1.040 (16H, m),0.857 (6H, d, J=6.4 Hz), 0.848 (3H, d, J=6.4 Hz), 0.831 (3H, d, J=6.8Hz)

EXAMPLE 2682-Acetamido-1,3-diacetoxy-(3,7,11-trimethyl-2,6,10-tridecenyl)propane

¹ H-NMR (CDCl₃) δ: 5.57 (1H, br.s), 5.07 (3H, m), 4.28 (4H, s), 2.60(2H, d, J=7.8 Hz), 2.01 (6H, s), 2.05-1.94 (8H, m), 1.94 (3H, s),1.70-1.57 (12H, m)

EXAMPLE 2692-Acetamido-1,3-diacetoxy-2-(11-methoxycarbonylundecyl)propane

melting point=49.5°-51.5° C.

IR ν: 3300, 2930, 2850, 1740, 1655, 1580, 1475, 1390, 1240, 1060 cm⁻¹

¹ H-NMR (CDCl₃) δ: 5.61 (1H, br.s), 4.265 (4H, dd, J=13.6 Hz, 11.2 Hz),3.635 (3H, s), 2.272 (2H, t, J=7.6 Hz), 2.051 (6H, s), 1.934 (3H, s),1.836-1.817 (2H, m), 1.225 (18H, br.s)

EXAMPLE 270 2-Acetamido-1,3-diacetoxy-(12-acetoxydodecyl)propane

melting point=67.5°-69.0° C.

¹ H-NMR (CDCl₃) δ: 5.607 (1H, br.s), 4.267 (4H, dd, J=13.7, 11.3 Hz),4.021 (2H, t, J=6.9 Hz), 2.052 (6H, s), 2.017 (3H, s), 1.934 (3H, s),1.840-1.819 (2H, m), 1.225 (2OH, br.s)

EXAMPLE 271 2-Amino-2-(1,2,12-trihydroxyoctadecyl)-1,3-propanediol

¹ H-NMR (400 MHz, in CD₃ OD) δ: 3.85-3.73 (7H, m), 1.60 (2H, m),1.45-1.25 (26H, 0.90 (3H, t)

IR ν_(max) (KBr): 3350(br), 2920, 2850, 1560, 1480, 1420, 1060 cm⁻¹

EXAMPLE 272 2-Amino-2-(1,2-dihydroxy-12-oxooctadecyl)-1,3-propanediol

¹ H-NMR (400 MHz, in CD₃ OD) δ: 5.48 (2H, m), 3.86-3.72 (6H, m), 2.44(4H, t), 2.29 (2H, t), 2.02 (2H, t), 1.53 (4H, quintet), 1.29 (12H,br.s), 0.89 (3H, t)

IR ν_(max) (CHCl₃): 3300, 2925, 2850, 1710, 1560, 1420, 1060, 980 cm⁻¹

EXAMPLE 2732-Amino-2-(1,2-dihydroxy-12-hydroxyiminooctadecyl)-1,3-propanediol

¹ H-NMR (400 MHz, in CD₃ OD) δ: 3.85-3.73 (4H, m), 2.42 (2H, t), 2.15(2H, t), 1.62-1.32 (24H, m), 0.89 (3H, t)

IR ν_(max) (CHCl₃): 3300(br), 2920, 2850, 1560, 1420, 1050 cm⁻¹

EXAMPLE 274 2-Amino-2-(1,2,12-trihydroxy-4-octadecenyl)-1,3-propanediol

A lactone compound (2.00 g) of2-amino-3-hydroxy-2-(1,2-dihydro-12-oxo-4-octadecenyl)propionic acid wasdissolved in 66 ml of dry tetrahydrofuran and 800 mg of lithium aluminumhydride was portionwise added thereto at room temperature with stirring.The mixture was stirred at room temperature for 40 minutes and 0.8 ml ofwater, 0.8 ml of a 15% aqueous sodium hydroxide solution and 2.4 ml ofwater were added thereto in order. The insoluble matters were filteredoff. The filtrate obtained was concentrated under reduced pressure, andthe residue was washed with water and dried under reduced pressure togive 408 mg of the subject compound.

IR ν_(max) (KBr): 3280, 2920, 2850, 1640, 1470, 1400, 1075, 970cm⁻¹

¹ H-NMR (300 MHz, in CD₃ OD, Ref:TMS) δ: 5.57 (1H, dt, J=15.3 and 6.6Hz), 5.43 (1H, dr, J=15.3 and 6.9 Hz), 3.85 (1H, dr, J=6.9 and 1.0 Hz),3.84-3.73 (5H, m), 3.67 (1H, d, J=1.0 Hz), 2.31 (2H, br.t, J=6.7 Hz),2.02 (2H, br.q, J=6.4 Hz), 1.42-1.31 (20H,m) 0.90 (3H, t, J=6.8 Hz)

EXAMPLE 275 2-Amino-2-(1,2-dihydroxy-4-octadecenyl)-1,3-propanediol

A lactone compound (978 mg) of2-amino-3-hydroxy-2-(1,2-dihydroxy-4-octadecenyl)propionic acid and 403mg of lithium aluminum hydride were reacted in 33 ml of drytetrahydrofuran according to the method of Example 274 to give 222 mg ofthe subject compound.

IR ν_(max) (KBr) cm⁻¹ : 3300, 2920, 2850, 1575, 1480, 1390, 1060, 1105,975

¹ H-NMR (200 MHz, in CD₃ OD, Ref:TMS) δ: 5.57 (1H, dt, J=15.4 and 6.4Hz), 5.42 (1H, dt, J=15.4 and 6.5 Hz), 3.88-3.66 (6H, m), 2.31 (2H, t,J=6.7 Hz), 2.04-1.93 (2H, m), 1.28 (22H, br.s), 0.90 (t, J=6.5 Hz)

EXAMPLE 276 2-Amino-2-(1,2-dihydroxyoctadecyl)-1,3-propanediol

2-Amino-2-(1,2-dihydroxy-4-octadecenyl)-1,3-propanediol (68.0 mg) wasdissolved in 14 ml of methanol and 6.8 mg of 5% palladium-carbon wasadded thereto. The catalytic reduction was conducted at ordinarytemperature and at atmospheric pressure day and night. After thereaction, the catalyst was filtered off and the filtrate wasconcentrated under reduced pressure to give 34.3 mg of the subjectcompound.

IR ν_(max) (KBr) cm⁻¹ : 3300, 2920, 2850, 1575, 1460, 1370, 1060

¹ H-NMR (200 MHz, in CD₃ OD, Ref:TMS) δ: 3.77 (6H, m), 1.65 (2H, m),1.27 (28H, br.s), 0.89 (3H, t, J=6.5 Hz)

EXAMPLE 277 2-Amino-2-(1,12-dihydroxy-4-octadecenyl)-1,3-propanediol

According to the method of Example 274, 35.0 mg of2-amino-3-hydroxy-2-(1-hydroxy-12-oxo-4-octadecenyl)propionic acid and14.4 mg of lithium aluminum hydride were reacted in 2.0 ml of drytetrahydrofuran to give 8.9 mg of the subject compound.

IR ν_(max) (KBr) cm⁻¹ : 3300, 2920, 2850, 1640, 1400, 970

¹ H-NMR (200 MHz, in CD₃ OD, Ref:TMS) δ: 5.40 (2H, m), 3.97-3.70 (5H,m), 3.58 (1H, m), 1.94 (4H, m), 1.70-1.21 (22H, m), 0.88 (3H, t, J=6.5Hz)

In the same manner as above, the following compounds are obtained.

EXAMPLE 278 2-Amino-2-(1,2,12-trihydroxyoctadecyl)-1,3-propanediolEXAMPLE 279 2-Amino-2-(1,12-dihydroxyoctadecyl)-1,3-propanediol EXAMPLE280 2-Amino-2- 2-(4-heptyloxyphenyl)ethyl!-1,3-propanediol

(1) 2-(4-Heptyloxyphenyl)ethanol

2-(4-Hydroxyphenyl)ethanol (10.0 g) and sodium methoxide (4.30 g) wereadded to methanol (120 ml) and the mixture was refluxed under heatingfor 30 minutes. A solution of heptyl bromide (14.2 g) in methanol (30ml) was dropwise added thereto and the mixture was refluxed underheating for 6 hours with stirring. The reaction mixture was concentratedand the concentrate was poured into ice water. The mixture was extractedwith ethyl acetate. The ethyl acetate layer was washed with saturatedbrine and dried over magnesium sulfate. The solvent was distilled awayand the resultant residue was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:2) to give the subjectcompound (10.81 g).

melting point=37°-39° C.

Rf value: 0.44 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.0 Hz), 1.10-1.99 (11H, m), 2.81 (2H,t, J=6.25 Hz), 3.68-4.05 (4H, m), 6.85 (2H, d, J=8.7 Hz), 7.15 (2H, d,J=8.7 Hz)

IR: 3312, 1610, 1514, 1249 cm⁻¹

MS(EI): 236(M⁺)

(2) 2-(4-Heptyloxyphenyl)ethylmethanesulfonate

Triethylamine (4.2 g) was added to a solution of the above-mentionedcompound (10.81 g) in tetrahydrofuran (300 ml) and the mixture wascooled with ice. Methanesulfonyl chloride (5.23 g) was dropwise addedthereto and the mixture was stirred at room temperature for 2 hours. Thereaction mixture was poured into ice water and extracted withdichloromethane. The dichloromethane layer was washed with a saturatedpotassium hydrogencarbonate solution, a 1% aqueous hydrochloric acidsolution and saturated brine and dried over magnesium sulfate. Thesolvent was distilled away and the resultant residue was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:5) togive the subject compound (11.32

melting point=35°-36° C.

Rf value: 0.33 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.90 (3H, t, J=6.0 Hz), 1.10-1.95 (10H, m), 2.86 (3H,3.00 (2H, t, J=7.5 Hz), 3.94 (2H, t, J=6.3 Hz), 4.39 (2H, t, J=7.0 Hz),6.85 (2H, d, J=8.7 Hz), 7.15 (2H, d, J=8.7 Hz)

IR: 1354, 1516, 1249cm⁻¹

MS(EI): 314(M⁺)

(3) 2-(4-Heptyloxyphenyl)ethyl iodide

Sodium iodide (10 g) was added to a solution of the above-mentionedcompound (11.32 g) in 2-butanone (400 ml) and the mixture was refluxedunder heating for 4 hours. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over magnesium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gel.column chromatography (eluent; ethyl acetate:hexane=1:5) to give thesubject compound (9.07 g).

Rf value: 0.80 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.0 Hz), 1.10-1.96 (10H, m), 2.98-3.48(4H, m), 3.94 (2H, t, J=6.3 Hz), 6.84 (2H, d, J=8.7 Hz), 7.11 (2H, d,J=8.7 Hz)

IR: 1610, 1512, 1246 cm⁻¹

MS(EI): 346(M⁺)

(4) Diethyl 2-acetamido-2-(4-heptyloxyphenyl)ethylmalonate

A solution of sodium ethoxide (4.99 g) in absolute ethanol (60 ml) wasdropwise added to diethyl acetamidomalonate (15 g) in a stream ofnitrogen and the mixture was stirred at 65° C. for 30 minutes. Asolution of the above-mentioned compound (8.0 g) in tetrahydrofuran (30ml) was dropwise added thereto and the mixture was stirred at 65° C. for6 hours. The reaction mixture was concentrated, poured into ice waterand extracted with ethyl acetate. The ethyl acetate layer was washedwith saturated brine and dried over anhydrous magnesium sulfate. Thesolvent was distilled away and the resultant residue was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:5) togive the subject compound (6.50 g).

melting point=77°-80° C.

Rf value: 0.44 (chloroform:methanol=9:1)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.0 Hz), 1.05-1.90 (16H, m), 1.98 (3H,s), 2.10-2.85 (4H, m), 3.92 (2H, t, J=7.0 Hz), 4.21 (4H, q, J=7.5 Hz),6.65 (1H, br.s), 6.79 (2H, d, J=8.7 Hz), 7.05 (2H, d, J=8.7 Hz)

IR: 3242, 1745, 1641, 1614, 1512, 1296 cm⁻¹

MS(EI): 435(M⁺)

(5) 1,3-Propanediyl-2-acetamido-2-2-(4-heptyloxyphenyl)ethyl!ylidenediacetate

A solution (50 ml) of the above-mentioned compound (6.50 g) in anhydroustetrahydrofuran was dropwise added to a solution (150 ml) of lithiumaluminum hydride (1.70 g) in anhydrous tetrahydrofuran under ice-coolingin a stream of nitrogen and the mixture was stirred at room temperaturefor 2 hours saturated aqueous sodium sulfate solution was added to thereaction mixture under ice-cooling and aluminum hydroxide produced wasfiltered off. The solvent was distilled away and pyridine (66 ml) wasadded to the residue. Acetic anhydride (14 ml) was added thereto underice-cooling and the mixture was allowed to stand at room temperatureovernight. The reaction mixture was poured into ice-cooled 5%hydrochloric acid and the mixture was extracted with ethyl acetate. Theethyl acetate layer was washed with saturated brine and dried overanhydrous magnesium sulfate. The solvent was distilled away and theresidue obtained was purified by silica gel column chromatography(eluent; ethyl acetate) to give the subject compound (4.54 g) as whitecrystals.

melting point=89-91° C.

Rf value: 0.35 (chloroform:methanol=9:1)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.0 Hz), 1.05-2.72 (14H, m), 1.95 (3H,s), 2.08 (6H, s), 3.92 (2H, t, J=7.0 Hz), 4.34 (4H, s), 5.65 (1H, br.s),6.80 (2H, d, J=8.7 Hz), 7.10 (2H, d, J=8.7 Hz)

IR: 3308, 1739, 1651, 1614, 1514, 1246 cm⁻¹

MS(EI): 435(M⁺)

(6) 2-Amino-2- 2-(4-heptyloxyphenyl)ethyl!-1,3-propanediol hydrochloride

An aqueous solution (100 ml) of lithium hydroxide (3.93 g) was added toa solution of the above-mentioned compound (4.54 g) in methanol (70ml)-tetrahydrofuran (70 ml) and the mixture was refluxed under heatingfor 3 hours. The reaction mixture was concentrated and extracted withethyl acetate. The ethyl acetate layer was washed with saturated brineand dried over anhydrous magnesium sulfate. The solvent was distilledaway and the resultant mixture was recrystallized from ethyl acetate. A1M hydrochloric acid-ether solution (43 ml) was added to a solution ofthe resultant crystals in tetrahydrofuran (28 ml) methanol (28 ml). Thesolvent was distilled away and the crystals precipitated wererecrystallized from ethyl acetate to give the subject compound (1.30 g).

melting point: 111°-112° C.

Rf value: 0.20 (chloroform:methanol: 5:1)

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=5.5 Hz), 1.10-1.91 (14H, m), 3.56 (4H,t, J=5.0 Hz), 5.36 (2H, t, J=4.5 Hz), 6.84 (2H, d, J=8.7 Hz), 7.13 (2H,d, J=8.7 Hz), 7.85 (2H, br.s)

IR: 3279, 1610, 1514, 1246 cm⁻¹

MS(EI): 309(M⁺)

elemental analysis: calculated C 62.50, H 9.32, N 4.05 found C 62.06, H9.11, N 4.13

EXAMPLE 281 2-Amino-2- 2-(4-nonyloxyphenyl)ethyl!-1,3-propanediol

(1) 2-(4-Nonyloxyphenyl)ethanol

2-(4-Hydroxyphenyl)ethanol (10.0 g) and sodium methoxide (4.30 g) wereadded to methanol (120 ml) and the mixture was refluxed under heatingfor 30 minutes. A solution of nonyl bromide (33 g) in methanol (20 ml)was dropwise added thereto and the mixture was refluxed under heatingfor 6 hours. The reaction mixture was concentrated, poured into icewater and extracted with ethyl acetate. The ethyl acetate layer waswashed with saturated brine and dried over magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:3) togive the subject compound (20 g).

Rf value: 0.46 (ethyl acetate:n-hexane=1:2)

(2) 2-(4-Nonyloxyphenyl)ethylmethanesulfonate

Triethylamine (8.8 g) was added to a solution of the above-mentionedcompound (20 g) in tetrahydrofuran (500 ml) and the mixture was cooledwith ice. Methanesulfonyl chloride (9.17 g) was dropwise added theretoand the mixture was stirred at room temperature for 4 hours. Thereaction mixture was poured into ice water and extracted withdichloromethane. The dichloromethane layer was washed with a saturatedpotassium hydrogencarbonate solution, a 1% aqueous hydrochloric acidsolution and saturated brine and dried over magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:3) togive the subject compound (19.6 g).

melting point=37-42° C.

Rf value: 0.45 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.9 Hz), 1.05-1.90 (16H, m), 2.82 (3H,s), 2.99 (2H, t, J=6.1 Hz), 3.90 (2H, t, J=6.9 Hz), 4.35 (2H, t, J=6.9Hz), 6.78 (2H, d, J=8.3 Hz), 7.06 (2H, d, J=8.3 Hz)

IR: 1354, 1251 cm⁻¹

MS(EI): 342(M⁺)

(3) 2-(4-Nonyloxyphenyl)ethyl iodide

Sodium iodide (17 g) was added to a solution of the above-mentionedcompound (19.6 g) in 2-butanone (650 ml) and the mixture was refluxedunder heating for 4 hours. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over magnesium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:3) to give thesubject compound (18.08 g) as an oily substance.

Rf value: 0.69 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.90 (3H, t, J=5.5 Hz), 1.05-1.90 (14H, m), 2.90-3.40(4H, m), 3.90 (2H, t, J=6.9 Hz), 6.76 (2H, d, J=8.3 Hz), 7.02 (2H, d,J=8.3 Hz)

IR: 1610, 1512, 1246 cm⁻¹

MS(EI): 374(M⁺)

(4) Diethyl 2-acetamido-2-(4-nonyloxyphenyl)ethylmalonate

A solution of sodium ethoxide (10.4 g) in absolute ethanol (135 ml) wasdropwise added to diethyl acetamidomalonate (31 g) in a stream ofnitrogen and the mixture was stirred at 65° C. for 30 minutes. Asolution of the above-mentioned compound (18 g) in tetrahydrofuran (63ml) was dropwise added thereto and the mixture was stirred at 65° C. for6 hours. The reaction mixture was concentrated, poured into ice waterand extracted with ethyl acetate. The ethyl acetate layer was washedwith saturated brine and dried over anhydrous magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:3) togive the subject compound (8.78 g).

melting point=76°-77° C.

Rf value: 0.38 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.8 Hz), 1.05-1.80 (20H, m), 1.99 (3H,s), 2.20-2.75 (4H, m), 3.88 (2H, t, J=6.2 Hz), 4.15 (4H, q, J=6.9 Hz),6.70 (1H, br.s), 6.72 (2H, d, J=8.3 Hz), 6.99 (2H, d, J=8.3 Hz)

IR: 3281, 1743, 1645, 1512, 1246 cm⁻¹

MS(EI): 463(M⁺)

(5) 1,3-Propanediyl-2-acetamido-2-2-(4-nonyloxyphenyl)ethyl!ylidenediacetate

A solution (50 ml) of the above-mentioned compound (8.78 g) in anhydroustetrahydrofuran was dropwise added to a solution (150 ml) of lithiumaluminum hydride (1.79 g) in anhydrous tetrahydrofuran under ice-coolingin a stream of nitrogen and the mixture was stirred at room temperaturefor 2 hours. A saturated aqueous sodium sulfate solution was added tothe reaction mixture under ice-cooling and aluminum hydroxide producedwas filtered off. The solvent was distilled away and pyridine (84 ml)was added to the residue. Acetic anhydride (18 ml) was added theretounder ice-cooling and the mixture was allowed to stand at roomtemperature overnight. The reaction mixture was poured into ice-cooled5% hydrochloric acid and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue obtained waspurified by silica gel column chromatography (eluent; ethyl acetate) togive the subject compound (5.62 g) as white crystals.

melting point=88°-94° C.

Rf value: 0.50 (chloroform:methanol=9:1)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.9 Hz), 1.05-2.30 (18H, m), 1.93 (3H,s), 2.06 (6H, s), 3.89 (2H, t, J=7.0 Hz), 4.30 (4H, s), 5.60 (1H, br.s),6.72 (2H, d, J=8.2 Hz), 7.01 (2H, d, J=8.2 Hz)

IR: 3308, 1738, 1651, 1614, 1514, 1246 cm⁻¹

MS(EI): 463(M⁺)

elemental analysis: calculated C 67.36, H 8.91, N 3.02 found C 67.35, H8.777 N 3.05

(6) 2-Amino-2- 2-(4-nonyloxyphenyl)ethyl!-1,3-propanediol hydrochloride

An aqueous solution (54 ml) of lithium hydroxide (4.57 g) was added to asolution of the above-mentioned compound (5.62 g) in methanol (86ml)-tetrahydrofuran (86 ml) and the mixture was refluxed under heatingfor 3 hours. The reaction mixture was concentrated and extracted withethyl acetate. The ethyl acetate layer was washed with saturated brineand dried over anhydrous magnesium sulfate. The solvent was distilledaway and the residue was crystallized from ethyl acetate. A 1Mhydrochloric acid/ether solution (20 ml) was added to a solution of theresultant crystals in tetrahydrofuran (40 ml)-methanol (40 ml). Thesolvent was distilled away and crystals precipitated were recrystallizedfrom ethyl acetate to give the subject compound (2.10 g).

melting point=106°-108° C.

Rf value: 0.14 (chloroform:methanol=5:1)

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=4.1 Hz), 1.10-1.90 (18H, m), 3.50 (4H,d, J=4.7 Hz), 3.88 (2H, t, J=5.4 Hz), 5.32 (2H, t, J=4.9 Hz), 6.75 (2H,d, J=8.2 Hz), 7.02 (2H, d, J=8.2 Hz), 7.81 (2H, br.s)

IR: 3277, 1610, 1514, 1248 cm⁻¹

MS(EI): 337(M⁺)

elemental analysis: calculated C 64.24, H 9.70, N 3.75 found C 64.16, H9.51, N 3.70

EXAMPLE 282 2-Amino-2-2-(4-(N-heptyl-N-methylamino)phenyl)ethyl!-1,3-propanediol

(1) 2-(4-Heptanoylaminophenyl)ethanol

2-(p-Aminophenyl)ethyl alcohol (13.8 g) and triethylamine (10.8 g) wereadded to tetrahydrofuran (300 ml) and the mixture was stirred for 30minutes under ice-cooling. Heptanoyl chloride (15 g) was dropwise addedthereto, and the mixture was stirred for 30 minutes under ice-coolingand then at room temperature for 3 hours. The reaction mixture waspoured into ice water and extracted with ethyl acetate. The ethylacetate layer was washed with saturated brine and dried over magnesiumsulfate. The solvent was distilled away and the residue obtained wasrecrystallized from ethyl acetate-isopropyl alcohol to give the subjectcompound (13.15 g).

melting point=105°-110° C.

Rf value: 0.41 (ethyl acetate:n-hexane=1:2→1:1)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.8 Hz), 1.31-1.42 (8 H, m), 1.70 (2H,tt, J=7.3 Hz, J=7.8 Hz), 2.35 (2H, t, J=7.3 Hz), 2.83 (2H, t, J=6.4 Hz),3.84 (2H, dd, J=6.3 Hz, J=5.8 Hz), 7.12 (1H, br.s), 7.18 (2H, dd, J=8.3Hz), 7.45 (2H, d,J=8.3 Hz)

IR: 3302, 1660, 1593, 1412 cm⁻¹

MS(EI): 249(M⁺)

elemental analysis: calculated C 70.97, H 9.33, N 5.52 found C 71.30, H9.26, N 5.66

(2) 2-(4-Heptanoylaminophenyl)ethoxytetrahydropyran

The above-mentioned compound (7.0 g), 3,4-dihydro-2H-pyran (3.08 g) andp-toluenesulfonic acid (180 mg) were added to tetrahydrofuran (50 ml)and dichloromethane (50 ml), and the mixture was stirred at roomtemperature for 7 hours. Triethylamine (0.5 ml) was added thereto andthe solvent was distilled away. The resultant residue was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:1) togive the subject compound (11 g).

melting point: 66°-68° C.

Rf value: 0.72 (ethyl acetate:n-hexane: 1:1)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.4 Hz), 1.31-2.05 (14H, m), 2.34 (2H,t, J=7.3 Hz), 2.87 (2H, t, J=6.4 Hz), 3.47 (2H, t, J=6.4 Hz), 3.47 (2H,dt, J=7.3 Hz, J=9.7 Hz), 3.77 (1H, m), 3.92 (1H, dt, J=7.3 Hz, J=9.8Hz), 4.58 (1H, t, J=3.9 Hz), 7.19 (2H, d, J=8.3 Hz), 7.42 (2H, d, J=8.3Hz)

IR: 3273, 1655, 1599, 1033 cm⁻¹

MS(EI): 333(M⁺)

(3) 2-(4-(N-Heptanoyl-N-methylamino)phenyl)ethoxytetrahydropyran

The above-mentioned compound (7.0 g) and potassium-t-butoxide (5.18 g)were added to ethylene glycol dimethyl ether (120 ml) and the mixturewas stirred at 60° C. for 30 minutes. A solution of methyl iodide (16.39g) in ethylene glycol dimethyl ether (4 ml) was added thereto and themixture was stirred at 60° C. for 1 hour. The solvent was distilled awayand the residue obtained was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:7) to give the subjectcompound (5.95 g).

Rf value: 0.23 (ethyl acetate:n-hexane=1:5)

¹ H-NMR (CDCl₃) δ: 0.83 (3H, t, J=6.8 Hz), 1.17-1.26 (6H, m), 1.42-1.60(4H, m), 1.63-1.90 (4H, m), 2.04 (2H, t, J=6.4 Hz), 3.47 (2H, t, J=6.4Hz), 3.47 (2H, dr, J=7.3 Hz, J=9.7 Hz), 3.77 (1H, m), 3.92 (1H, dr,J=7.3 Hz, J=9.8 Hz), 4.58 (1H, t, J=3.9 Hz), 7.19 (2H, d, J=8.3 Hz),7.42 (2H, d, J=8.3 Hz)

IR: 3273, 1655, 1599, 1033 cm⁻¹

MS(EI): 333(M⁺)

(4) 2-(4-(N-Heptyl-N-methylamino)phenyl)ethoxytetrahydropyran

A solution of the above-mentioned compound (5.95 g) in tetrahydrofuran(90 ml) was cooled to 5° C. and a diboranetetrahydrofuran complex(tetrahydrofuran 1M solution: 32.2 ml) was added thereto. The mixturewas stirred at 5° C. for 3 hours and methanol (60 ml) was added thereto.The solvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:7) togive the subject compound (3.6 g).

Rf value: 0.49 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=7.3 Hz), 1.22-1.40 (8H, m), 1.42-1.62(8H, m), 1.68-1.84 (2H, m), 2.81 (2H, t, J=7.3 Hz), 2.89 (3H, s), 3.26(2H, t, J=7.8 Hz), 3.46 (1H, m), 3.57 (1H, dr, J=7.4 Hz, J=7.8 Hz), 3.81(1H, m), 3.89 (1H, dr, J=7.3 Hz, J=7.8 Hz), 4.60 (1H, t, J=3.0 Hz), 6.63(2H, d, J=8.8 Hz), 7.08 (2H, d, J=8.8 Hz)

IR: 1616, 1365, 1030 cm⁻¹

MS(EI): 333(M⁺)

(5) 2-(4-(N-Heptyl-N-methylamino)phenyl)ethyl alcohol

p-Toluenesulfonic acid (3.10 g) was added to a solution of theabove-mentioned compound (3.36 g) in methanol (60 ml) and the mixturewas stirred at room temperature for 3 hours. Triethylamine (3 ml) wasadded thereto and the solvent was distilled away. The residue obtainedwas purified by silica gel column chromatography (eluent; ethylacetate:hexane=1:12) to give the subject compound (3.22 g).

Rf value: 0.31 (methanol:chloroform=1:9)

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6.9 Hz), 1.22-1.38 (10H, m), 2.77 (2H,t, J=6.4 Hz), 2.90 (3H, s), 3.27 (2H, t, J=7.4 Hz), 3.80 (1H, t, J=6.4Hz), 6.66 (2H, d, J=8.7 Hz), 7.08 (2H, d, J=8.7 Hz)

IR: 3368, 1369 cm⁻¹

MS(EI): 249(M⁺)

(6) 2-(4-(N-Heptyl-N-methylamino)phenyl)ethylmethanesulfonate

Triethylamine (2.22 g) was added to a solution of the above-mentionedcompound (3.65 g) in tetrahydrofuran (60 ml) and the mixture was cooledwith ice. Methanesulfonyl chloride (3.01 g) was dropwise added theretoand the mixture was stirred at room temperature for 2 hours. Thereaction mixture was poured into ice water and extracted withdichloromethane. The dichloromethane layer was washed with a saturatedpotassium hydrogencarbonate solution, a 1% aqueous hydrochloric acidsolution and saturated brine and dried over magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:5) togive the subject compound (4.02 g).

Rf value: 0.56 (ethyl acetate:n-hexane=1:5)

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6.4 Hz), 1.24-1.29 (10H, m), 2.84 (3H,s), 2.90 (3H, s), 2.96 (2H, t, J=6.8 Hz), 3.27 (2H, t, J=7.3 Hz), 4.36(2H, t, J=6.9 Hz), 6.64 (2H, d, J=8.3 Hz), 7.07 (2H, d, J=8.3 Hz)

(7) 2-(4-(N-heptyl-N-methylamino)phenyl)ethyl iodide

Sodium iodide (3.66 g) was added to a solution of the above-mentionedcompound (4.00 g) in 2-butanone (200 ml) and the mixture was refluxedunder heating for 2 hours. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over magnesium sulfate. The solvent wasdistilled away and the resultant residue was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:10) to give thesubject compound (2.58 g) as an oily substance.

Rf value: 0.78 (ethyl acetate:n-hexane=1:10)

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=7.3 Hz), 1.22-1.40 (10H, m), 2.90 (2H,s), 3.07 (2H, t, J=7.8 Hz), 3.63 (2H, t, J=5.9 Hz), 3.65 (2H, t, J=7.3Hz), 6.62 (2H, d, J=8.3 Hz), 7.04 (2H, d, J=8.3 Hz)

IR: 1614, 1521, 1371, 804 cm⁻¹

MS(EI): 359(M⁺)

(8) Diethyl2-acetamide-2-(4-(N-heptyl-N-methylamino)phenyl)ethylmalonate

A solution of sodium ethoxide (1.54 g) in absolute ethanol (18 ml) wasdropwise added to diethyl acetamidomalonate (4.63 g) in a stream ofnitrogen and the mixture was stirred at 60° C. for 30 minutes. Asolution of the above-mentioned compound (18 g) in tetrahydrofuran (7ml) was dropwise added thereto and the mixture was stirred at 60° C. for6 hours. The reaction mixture was concentrated, poured into ice waterand extracted with ethyl acetate. The ethyl acetate layer was washedwith saturated brine and dried over anhydrous magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:2) togive the subject compound (1.92 g) as an oily substance.

Rf value: 0.49 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6.8 Hz), 1.23-1.29 (10H, m), 1.24 (6H,t, J=7.4 Hz), 1.99 (3H, s), 2.38 (2H, m), 2.63 (2H, m), 2.88 (3H, s),3.25 (2H, t, J=7,3 Hz), 4.21 (4H, q, J=7.4 Hz), 6.60 (2H, d, J=8.3 Hz),6.76 (1H, br.s), 6.99 (2H,d, J=8.3 Hz)

IR: 3285, 1739, 1682, 1616, 1371 cm⁻¹

MS(EI): 448(M⁺)

(9) 1,3-Propanediyl-2-acetamide-2-2-(4-(N-heptyl-N-methylamino)phenyl)ethyl!ylidenediacetate

A solution (20 ml) of the above-mentioned compound (1.92 g) in anhydroustetrahydrofuran was added dropwise to a solution (35 ml) of lithiumaluminum hydride (0.49 g) in anhydrous tetrahydrofuran under ice-coolingin a stream of nitrogen. The mixture was stirred at room temperature for2 hours. A saturated aqueous sodium sulfate solution was added to thereaction mixture under ice-cooling and aluminum hydroxide produced wasfiltered off. The solvent was distilled away and pyridine (84 ml) wasadded to the residue. Acetic anhydride (19 ml) was added thereto underice-cooling and the mixture was allowed to stand at room temperatureovernight. The reaction mixture was poured into ice-cooled 5%hydrochloric acid and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue obtained waspurified by silica gel column chromatography (eluent; ethyl acetate) togive the subject compound (1.2 g) as an oily substance.

melting point=88°-94° C.

Rf value: 0.50 (chloroform:methanol=9:1)

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6.9 Hz), 1.24-1.29 (10H, m), 1.94 (3H,s), 2.08 (6H, s), 2.15 (2H, m), 2.51 (2H, m), 2.89 (3H, s), 3.26 (2H, t,J=7.8 Hz), 4.36 (4H, s), 5.60 (1H, br.s), 6.63 (2H, d, J=8.3 Hz), 7.03(2H, d, J=8.3 Hz)

IR:3314, 1739, 1651, 1616, 1386 cm⁻¹

MS(EI): 448(M⁺)

(10) 2-Amino-2-2-(4-(N-heptyl-N-methylamino)phenyl)ethyl!-1,3-propanediol hydrochloride

An aqueous solution (12 ml) of lithium hydroxide (1.01 g) was added to asolution of the above-mentioned compound (1.20 g) in methanol (18ml)-tetrahydrofuran (18 ml) and the mixture was refluxed under heatingfor 3 hours. The reaction mixture was concentrated and extracted withethyl acetate. The ethyl acetate layer was washed with saturated brineand dried over anhydrous magnesium sulfate. The solvent was distilledaway and the residue was recrystallized from ethyl acetate. A 1Mhydrochloric acid/ether solution (14 ml) was added to a solution of theresultant crystals in tetrahydrofuran (7 ml)-methanol (7 ml). Thesolvent was distilled away and the crystals precipitated wererecrystallized from ethyl acetate to give the subject compound (0.11 g).

melting point=128°-129° C.

Rf value: 0.20 (chloroform:methanol=9:1)

¹ H-NMR (CDCl₃) δ: 0.84 (3H, t, J=6.8 Hz), 1.25-1.46 (10H, m), 1.70-1.74(2H, m), 2.42-2.46 (2H, m), 2.81 (3H, s), 3.23 (2H, t, J=7.4 Hz), 3.49(4H, d, J=5.3 Hz), 5.35 (2H, t, J=4.9 Hz), 6.59 (2H, d, J=8.3 Hz), 6.97(2H, d, J=8.3 Hz)

IR: 3277, 1610, 1514, 1248 cm⁻¹

MS(EI): 322(M⁺)

elemental analysis: calculated C 59.13, H 9.92, N 7.26 (1.5H₂ O) found C59.23, H 9.39, N 7.14

EXAMPLE 283 2-Amino-2- 2-(4-heptanoylaminophenyl)ethyl!-1,3-propanediol

(1) 2-(4-Heptanoylaminophenyl)ethanol

2-(p-Aminophenyl)ethyl alcohol (13.8 g) and triethylamine (10.8 g) wereadded to tetrahydrofuran (300 ml) and the mixture was stirred underice-cooling for 30 minutes. Heptanoyl chloride (15 g) was dropwise addedthereto and the mixture was stirred under ice-cooling for 30 minutes andthen at room temperature for 3 hours. The reaction mixture was pouredinto ice water and extracted with ethyl acetate. The ethyl acetate layerwas washed with saturated brine and dried over magnesium sulfate. Thesolvent was distilled away and the resultant residue was recrystallizedfrom ethyl acetate-isopropyl alcohol to give the subject compound (13.15g).

melting point=105°-110° C.

Rf value: 0.41 (ethyl acetate:n-hexane=1:2→1:1)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.8 Hz), 1.31-1.42 (8H, m), 1.70 (2H,tt, J=7.3 Hz, J=7.8 Hz), 2.35 (2H, t, J=7.3 Hz), 2.83 (2H, t, J=6.4 Hz),3.84 (2H, dd, J=6.3 Hz, J=5.8 Hz), 7.12 (1H, br.s), 7.18 (2H, d, J=8.3Hz), 7.45 (2H, d,J=8.3 Hz)

IR: 3302, 1660, 1593, 1412 cm⁻¹

MS(EI): 249(M⁺)

elemental analysis: calculated C 70.97, H 9.33, N 5.52 found C 71.30, H9.26, N 5.66

(2) 2-(4-Heptanoylaminophenyl)ethylmethanesulfonate

Triethylamine (3.67 g) was added to the above-mentioned compound (6.00g) in tetrahydrofuran (100 ml) and the mixture was cooled with ice.Methanesulfonyl chloride (5.00 g) was dropwise added thereto and themixture was stirred at room temperature for 2 hours. The reactionmixture was poured into ice water and extracted with dichloromethane.The dichloromethane layer was washed with a saturated potassiumhydrogencarbonate solution, a 1% aqueous hydrochloric acid solution andsaturated brine and dried over magnesium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:1) to give thesubject compound (6.02 g).

melting point=103°-105° C.

Rf value: 0.56 (ethyl acetate:n-hexane=1:5)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.4 Hz), 1.22-1.40 (6H, m), 1.72 (2H,t, J=7.3 Hz), 2.35 (2H, t, J=7.3 Hz), 2.87 (3H, s), 3.02 (2H, t, J=7.3Hz), 4.39 (2H, t, J=6.4 Hz), 7.13 (1H, br.s), 7.19 (2H, d, J=8.3 Hz),7.48 (2H, d, J=8.3 Hz)

IR: 3307. 1659, 1337 cm⁻¹

MS(EI): 327(M⁺)

elemental analysis: calculated C 70.97, H 9.33, N 5.52 found C 71.30, H9.26, N 5.66

(3) 2-(4-Heptanoylaminophenyl)ethyl iodide

Sodium iodide (5.51 g) was added to a solution of the above-mentionedcompound (6.02 g) in 2-butanone (300 ml) and the mixture was refluxedunder heating for 2 hours. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over magnesium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:5) to give thesubject compound (5.31 g) as an oily substance.

melting point=82°-86° C.

Rf value: 0.33 (ethyl acetate:n-hexane=1:5)

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6.9 Hz), 1.21-1.40 (6H, m), 1.70 (2H,t, J=7.3 Hz), 2.32 (2H, t, J=7.3 Hz), 3.12 (2H, t, J=7.8 Hz), 3.30 (2H,t, J=7.4 Hz), 7.05 (1H, br.s), 7.12 (2H, d, J=8.3 Hz), 7.44 (2H, d,J=8.3 Hz)

IR: 3450, 1660, 1595, 709 cm⁻¹

MS(EI): 359(M⁺)

elemental analysis: calculated C 50.15, H 6.17, N 3.96 found C 50.11, H6.06, N 3.96

(4) Diethyl-2-tert-butoxycarbonylamino-2-(4-heptanoylaminophenyl)ethylmalonate

A solution of sodium ethoxide (3.19 g) in absolute ethanol (40 ml) wasdropwise added to diethyl 2-tert-butoxycarbonylaminomalonate (12.12 g)in a stream of nitrogen and the mixture was stirred at 50° C. for 30minutes. A solution of the above-mentioned compound (5.31 g) intetrahydrofuran (20 ml) was dropwise added thereto and the mixture wasstirred at 60° C. for 5 hours. The reaction mixture was concentrated,poured into ice water and extracted with ethyl acetate. The ethylacetate layer was washed with saturated brine and dried over anhydrousmagnesium sulfate. The solvent was distilled away and the residueobtained was purified by silica gel column chromatography (eluent; ethylacetate:hexane=1:7) to give the subject compound (4.29 g).

Rf value: 0.49 (ethyl acetate:n-hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.82 (3H, t, J=6.9 Hz), 1.18 (6H, t, J=6.8 Hz),1.21-1.40 (6H, m), 1.37 (9H, s), 1.64 (2H, t, J=7.4 Hz), 2.27 (2H, t,J=7.3 Hz), 2.42 (2H, m), 2.51 (2H, m), 4.05-4.25 (4H, m), 5.92 (1H,br.s), 7.00 (1H, br.s), 7.03 (2H, d, J=8.3 Hz), 7.33 (2H, d, J=8.3 Hz)

IR: 3319, 1772, 1739, 1666 cm⁻¹

MS(EI): 506(M⁺)

(5) 2-tert-Butoxycarbonyl-amino-2-2-(4-heptanoylaminophenyl)ethyl!-1,3-propanediol

Sodium borohydride (0.32 g) was added to a solution of theabove-mentioned compound (4.29 g) in methanol in a stream of nitrogen.The residue was purified by silica gel column chromatography (eluent;ethyl acetate:hexane=2:1) to give the subject compound (0.56.g) as anoily substance.

Rf value: 0.31 (acetic acid:n-hexane=2:1)

¹ H-NMR (CDCl₃) δ: 0.89 (3H, t, J=6.8 Hz), 1.21-1.46 (10H, m), 1.45 (9H,s), 1.70-1.90 (4H, m), 2.34 (2H, t, J=7.3 Hz), 2.59 (2H, t, J=8.7 Hz),3.61-3.64 (2H, m), 3.85-3.89 (2H, m), 5.03 (1H, br.s), 7.13 (2H, d,J=8.3 Hz), 7.42 (2H, d, J=8.3 Hz).

IR: 3310, 1668, 1602 cm⁻¹

MS(EI): 422(M⁺)

(6) 2-Amino-2- 2-(4-heptanoylaminophenyl)ethyl!-1,3-propanediol

A solution of the above-mentioned compound (0.56 g) in trifluoroaceticacid (4 ml) was stirred under ice-cooling for 4 hours. The reactionmixture was concentrated and ethyl acetate (110 ml) was added thereto.The mixture was washed with a saturated aqueous sodium hydrogencarbonatesolution and dried over anhydrous magnesium sulfate. The solvent wasdistilled away and the residue was recrystallized from methanol-ethylacetate to give the subject compound (0.14 g) as white crystals.

melting point=133°-135° C.

Rf value: 0.47 (chloroform:methanol=5:1)

¹ H-NMR (DMSO-d₆) δ: 0.85 (3H, t, J=6.4 Hz), 1.26-1.57 (12H, m), 2.25(2H, t, J=3.9 Hz), 3.17-3.25 (4H, m), 4.43 (2H, t, J=4.9 Hz), 7.07 (2H,d, J=8.8 Hz), 7.45 (2H, d,J=8.7 Hz), 9.73 (1H, br.s),

IR: 3317, 1653, 1601 cm⁻¹

MS(EI): 322(M⁺)

elemental analysis: calculated C 67.05, H 9.38, N 8.69 (1.5H₂ O) found C66.95, H 9.08, N 8.25

EXAMPLE 284 2-Amino-2- 2-(4-octylphenyl)ethyl!-1,3-propanediol

(1) Ethyl 2-ethoxycarbonyl-4-(4-octylphenyl)butyrate

Sodium (2.67 g) was dissolved in absolute ethanol (100 ml) and diethylmalonate (18.6 g) was dropwise added thereto at 27°-30° C. for 3minutes. The mixture was stirred at 40° C. for 40 minutes and2-(4-octylphenyl)ethyl iodide (40 g) was dropwise added to the reactionmixture at 44°-45° C. over 10 minutes. The mixture was refluxed at 50°C. for 1 hour and stirred under heating for 1.5 hours. The reactionmixture was cooled and the solvent was distilled away under reducedpressure. Water was added thereto and extracted with ethyl acetate. Theextract was washed with water and dried over magnesium sulfate. Thesolvent was distilled away under reduced pressure and the residueobtained was subjected to silica gel column chromatography to give thesubject compound (28.8 g).

IR: 2920, 2850, 1745, 1725, 1240, 1140, 1040 cm⁻¹

(2) Ethyl 2-amino-2-ethoxycarbonyl-4-(4-octylphenyl)butyrate

60% Sodium hydride (0.38 g) was suspended in dry dimethylformamide (30ml) and ethyl 2-ethoxycarbonyl-4-(4-octylphenyl)butyrate (3.0 g) wasadded thereto. The mixture was stirred at room temperature for 2 hours.O-(2,4-Dinitrophenyl)hydroxylamine (1.14 g) was added thereto and themixture was stirred at room temperature for 5 hours. The reactionmixture was poured into cool water and extracted with toluene. Theextract was washed with aqueous sodium chloride and dried over magnesiumsulfate. The solvent was distilled away under reduced pressure to give 3g of the subject compound.

IR: 3380, 3320, 2930, 2850, 1730, 1180 cm⁻¹

(3) 2-Amino-2- 2-(4-octylphenyl)ethyl!-1,3-propanediol

A suspension of sodium borohydride (0.60 g) and lithium bromide (1.66 g)in ethanol (17 ml) was stirred at room temperature for 25 minutes. Ethyl2-amino-2-ethoxycarbonyl-4-(4-octylphenyl)butyrate (1.24 g) was dropwiseadded thereto over 3 minutes and the mixture was stirred at roomtemperature for 5 hours. Water (40 ml) was added to the reaction mixtureand the mixture was stirred for 40 minutes. The crystals precipitatedwas collected by filtration and dried to give 0.68 g of the subjectcompound, melting point=125°-126° C. Treatment of the subject compoundwith hydrochloric acid-ethanol gives the corresponding hydrochloride.

EXAMPLE 285 2-Amino-2-{2- 4-(7-octenyloxy)phenyl!ethyl}-1,3-propanediol

(1) 2- 4-(7-Octenyloxy)phenyl!ethyl alcohol

Sodium ethoxide (4.98 g) was added to a solution (240 ml) of2-(4-hydroxyphenyl)ethyl alcohol (8.68 g) in absolute ethanol and themixture was stirred at 50° C. for 30 minutes. A solution of 7-octenylbromide (10 g) in anhydrous tetrahydrofuran was dropwise added theretoand the mixture was stirred at 50° C. for 6 hours. The reaction mixturewas concentrated, poured into ice water and extracted with ethylacetate. The ethyl acetate layer was washed with saturated brine anddried over anhydrous magnesium sulfate. The solvent was distilled awayand the residue was purified by silica gel chromatography (eluent; ethylacetate:hexane=1:5) to give the subject compound (10.76 g) as an oilysubstance.

¹ H-NMR (DMSO) δ: 1.35 (6H, s), 1.50-2.16 (4H, m), 2.62 (2H, t, J=6 Hz),3.41-3.68 (2H, m), 3.88 (2H, t, J=6 Hz), 4.63 (1H, t, J=5 Hz), 4.95 (2H,t×t, J=7 Hz, 2 Hz), 5.66-5.96 (1H, m), 6.74 (2H, d, J=9 Hz), 7.04 (2H,d, J=9 Hz)

IR ν NEAT_(max) : 3448, 2251, 1028, 823, 761cm⁻¹

MS 248 (M⁺)

(2) 2- 4-(7-Octenyloxy)phenyl!ethyl iodide

Triethylamine (7.25 ml) was added to a solution (100 ml) of theabove-mentioned compound (10.76 g) in dichloromethane and the mixturewas cooled with ice. Methanesulfonyl chloride (3.69 ml) was dropwiseadded thereto and the mixture was stirred at room temperature for 1hour. The reaction mixture was poured into ice water and extracted withchloroform. The chloroform layer was washed with saturated brine anddried over anhydrous magnesium sulfate. The solvent was distilled awayand sodium iodide (7.78 g) was added to a solution (200 ml) of theresidue in 2-butanone. The mixture was refluxed under heating for 5hours. The reaction mixture was concentrated, poured into ice water andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over anhydrous magnesium sulfate. The solventwas distilled away and the residue was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:3) to give the subjectcompound (13.72 g) as an oily substance.

¹ H-NMR (CDCl₃) δ: 1.53 (6H, s), 1.68-2.07 (4H, m), 2.96-3.18 (4H, m),3.90 (2H, t, J=6 Hz), 4.92 (2H, m), 5.56-5.96 (1H, m), 6.76 (2H, d, J=9Hz), 7.03 (2H, d, J=9 Hz)

IR ν NEAT_(max) : 2930, 1511, 1246cm⁻¹

MS 358 (M⁺)

(3) Diethyl 2-acetamido-2- 4-(7-octenyloxy)phenyl!ethylmalonate

Sodium ethoxide (5.72 g) was added to a solution (100 ml) of diethylacetamidomalonate (16.60 g) in absolute ethanol and the mixture wasstirred at 65° C. for 30 minutes. A solution (100 ml) of theabove-mentioned compound (13.69 g) in absolute ethanol was dropwiseadded thereto and the mixture was stirred at 65° C. for 3 hours. Thereaction mixture was concentrated, poured into ice water and extractedwith ethyl acetate. The ethyl acetate layer was washed with saturatedbrine and dried over anhydrous magnesium sulfate. The solvent wasdistilled away and the residue was purified by silica gel chromatography(eluent; ethyl acetate:hexane=1:2) to give the subject compound (4.60g).

melting point=50°-53° C.

¹ H-NMR (CDCl₃) δ: 1.25 (8H, t), 1.30-1.49 (6H, m), 1.72-1.79 (2H, m),2.00 (3H, s), 2.63-2.67 (2H, m), 3.91 (2H, t, J=6 Hz), 4.15-4.25 (4H,m), 4.92-5.03 (2H, m), 5.76-5.86 (1H, m), 6.79 (2H, d, J=8 Hz), 7.04(2H, d, J=8 Hz)

IR ν_(max) : 3251, 2931, 1743, 1515, 1247, 1186cm⁻¹

MS 447 (M⁺)

(4) 2-Acetamido-2- 2-{4-(7-octenyloxy)phenyl!ethyl!-1,3-propanedioldiacetate

A solution (70 ml) of the above-mentioned compound (4.47 g) in anhydroustetrahydrofuran was dropwise added to a solution (50 ml) of lithiumaluminum hydride (1.52 g) in anhydrous tetrahydrofuran underice-cooling. The mixture was heated to room temperature and stirred for3 hours. A saturated aqueous sodium sulfate solution was dropwise addedthereto under ice-cooling to decompose lithium aluminum hydride and thesame was filtered off. The reaction mixture was dried over anhydroussodium sulfate and the solvent was distilled away. Pyridine (19.8 ml)was added to the residue. Acetic anhydride (18.4 ml) was added theretounder ice-cooling and the mixture was allowed to stand at roomtemperature overnight. The reaction mixture was poured into ice waterand extracted with ethyl acetate. The ethyl acetate layer was washedwith 7% hydrochloric acid and saturated brine and dried over anhydrousmagnesium sulfate. The solvent was distilled away and the residue waspurified by silica gel chromatography (eluent; ethyl acetate:hexane=1:2)to give the subject compound (2.23 g) as white crystals.

melting point=88°-90° C.

MS 447 (M⁺)

¹ H-NMR (CDCl₃) δ: 1.54-1.57 (8H, m), 1.76 (2H, m), 1.96 (3H, s),2.03-2.09 (8H, m), 2.52-2.57 (2H, m), 3.92 (2H, t, J=6 Hz), 4.34 (4H,s), 4.93-5.02 (2H, m), 5.64 (1H, s), 5.64-5.86 (1H, m), 6.81 (2H, d, J=4Hz), 7.08 (2H, d, J=4 Hz)

IR ν : 3308, 1738, 1652, 1247, 1227 cm⁻¹

(5) 2-Amino-2-{2- 4-(7-octenyloxy)phenyl!ethyl}-1,3-propanediol

An aqueous solution (20 ml) of lithium hydroxide (0.84 g) was added to asolution (20 ml) of the above-mentioned compound (1.01 g) in methanoland the mixture was refluxed under heating for 2 hours. The reactionmixture was concentrated and extracted with ethyl acetate. The ethylacetate layer was washed with saturated brine and dried over anhydrousmagnesium sulfate. The solvent was distilled away and the residue wasrecrystallized from ethyl acetate to give the subject compound (0.32 g),melting point 95°-98° C.

¹ H-NMR (CDCl₃) δ: 1.36-1.48 (8H, m), 1.73-1.78 (2H, m), 2.06 (2H, q,J=8 Hz), 2.59 (2H, t, J=8 Hz), 3.56 (4H, q, J=12 Hz), 3.91 (2H, q, J=8Hz), 4.93-5.02 (2H, m), 5.76-5.86 (1H, 6.82 (2H, d, J=10 Hz), 7.09 (2H,t,J=10 Hz)

IR ν: 3350, 2938, 1512, 1245, 1021cm⁻¹

EXAMPLE 286 2-Amino-2- 2-(4-octyloxyphenyl)ethyl!-1,3-propanediolhydrochloride

(1) 2-Acetamido-2- 2-(4-octyloxyphenyl)ethyl!-1,3-propanediol diacetate

10% Palladium carbon (0.1 g) was added to a solution (30 ml) of2-acetamido-2- 2-{4-(7-octenyloxy)phenyl}ethyl!-1,3-propanedioldiacetate (1.27 g) in ethanol and the mixture was stirred at ordinarytemperature and at atmospheric pressure for 6 hours under a hydrogenatmosphere. The catalyst was filtered off and the filtrate wasconcentrated. The residue was collected by filtration to give thesubject compound (1.18 g).

melting point=99°-102° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=8 Hz), 1.26-1.56 (12H, m), 1.94 (3H,s), 2.07 (6H, s), 2.12-2.17 (2H, m), 2.50-2.55 (2H, m), 3.89 (2H, t, J=6Hz), 4.32 (4H, s), 5.62 (1H, s), 6.79 (2H, d, J=8 Hz), 7.06 (2H, d, J=8Hz)

IR ν: 3311, 2917, 1738, 1651, 1247 cm⁻¹

(2) 2-Amino-2-{2-(4-octyloxyphenyl)ethyl}-1,3-propanediol hydrochloride

An aqueous solution (20 ml) of lithium hydroxide (0.94 g) was added to asolution (20 ml) of the above-mentioned compound (1.13 g) in ethanol andthe mixture was refluxed under heating for 3 hours. The reaction mixturewas concentrated and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue was dissolved inmethanol (10 ml). A solution (10 ml) of 1M hydrochloric acid in etherwas added thereto and the crystals precipitated were collected byfiltration to give the subject compound (0.60 g, 65.2%).

melting point: 59°-61° C.

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=4 Hz), 1.28-1.41 (12H, m), 1.73-1.75(2H, m), 1.95(2H, m), 2.60 (2H, s), 3.78-3.92 (6H, m), 6.80 (2H, m),7.10 (2H, m)

IR ν: 3354, 1609, 1513, 1247 cm⁻¹

EXAMPLE 287 2-Amino-2-(13-phenyltridecyl)-1,3-propanediol

(1) 12-(Tetrahydropyran-2-yloxy)dodecanol

1,12-Dodecanediol (25 g) was dissolved in dichloromethane (200 ml) andtetrahydrofuran (200 ml), and a catalytic amount of p-toluenesulfonicacid and 3,4-dihydro-2H-pyran (14 ml) were added thereto. The mixturewas allowed to stand at room temperature for 2 hours and the reactionwas stopped by triethylamine. The solvent was distilled away and theresidue obtained was purified by silica gel column chromatography(eluent; ethyl acetate:hexane: 1:2) to give the subject compound (15.46g) as a colorless, oily-substance.

Rf value: 0.39 (ethyl acetate:hexane: 1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.28 (16H, m), 1.62 (10H, m), 3.65 (6H, m), 4.59(1H, br.s)

IR(neat): 3417, 2927, 2854, 1034cm⁻¹

MS(EI): 285 (M⁺ -1)

(2) 12-(Tetrahydropyran-2-yloxy)dodecanal

Oxalyl chloride (6.9 ml) was slowly added dropwise to a solution (85 ml)of dimethyl sulfoxide (11.3 ml) in dichloromethane at -78° C. under anitrogen atmosphere. The mixture was stirred at -78° C. for 20 minutesand a solution of the above-mentioned compound (15.25 g) indichloromethane (130 ml) was gradually added thereto over 30 minutes.The mixture was stirred at -78° C. for 20 minutes and triethylamine (37ml) was added thereto. The reaction was stopped with 150 ml of water andthe reaction mixture was extracted twice with 150 ml of chloroform. Thechloroform layer was dried and the solvent was distilled away. Theresidue obtained was purified by silica gel column chromatography(eluent; ethyl acetate:hexane=1:3) to give the subject compound (13.54g) as a slightly yellow, oily substance.

Rf value: 0.63 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.29 (14H, m), 1.58 (10H, m), 2.43 (2H, dr, J=2& 6 Hz), 3.26-4.20 (4H, m), 4.59 (1H, br.s), 9.79 (1H, t, J=2 Hz)

IR(neat): 2929, 2855, 1727cm⁻¹

MS(EI): 284 (M⁺)

(3) 1-Phenyl-13-(tetrahydropyran-2-yloxy)-1-tridecene

A solution (31 ml) of 1.6M butyl lithium in hexane was added to asuspension of benzyltriphenylphosphonium chloride (19.44 g) intetrahydrofuran (100 ml) under ice-cooling and a solution of theabove-mentioned compound (13.54 g) in tetrahydrofuran (30 ml) wasdropwise added thereto under ice-cooling. The mixture was stirred for 3hours. The reaction mixture was concentrated and the concentrate waspoured into 200 ml of ice water. The mixture was extracted twice with150 ml of ethyl acetate and the extract was dried and concentrated. Theresidue obtained was purified by silica gel column chromatography(eluent; ethyl acetate:hexane=1:9) to give the subject compound (2.60g).

Rf value: 0.66 (ethyl acetate:hexane=1:5)

¹ H-NMR (CDCl₃ /TMS) δ: 1.30 (14H, m), 1.58 (10H, m), 2.22 (2H, m), 3.60& 3.80 (4H, 2m), 4.59 (1H, br.s), 6.19-6.53 (2H, m), 7.30 (5H, m)

IR(neat): 2927, 2854, 1466, 1034 cm⁻¹

MS(EI): 358 (M⁺)

(4) 13-Phenyl-1-(tetrahydropyran-2-yloxy)tridecane

10% Palladium carbon (260 mg) was added to a solution of theabove-mentioned compound (2.63 g) in ethanol (80 ml) and the mixture wasstirred at room temperature for 3 hours under a hydrogen atmosphere. Thecatalyst was filtered through Celite and the filtrate was concentrated.The residue obtained was purified by silica gel column chromatography(eluent; ethyl acetate:hexane=1:9) to give the subject compound (2.67 g)as a colorless, oily substance.

Rf value: 0.60 (ethyl acetate:hexane=1:5)

¹ H-NMR (CDCl₃ /TMS) δ: 1.27 (18H, m), 1.60 (10H, m), 2.62 (2H, t, J=7Hz), 3.45 & 3.80 (4H, 2m), 4.59 (1H, br.s), 7.21 (5H, m)

IR(neat): 2927, 2854, 1453 cm⁻¹

MS(EI): 360 (M⁺)

(5) 13-Phenyltridecanol

A solution of the above-mentioned compound (2.63 g) and a catalyticamount of p-toluenesulfonic acid in methanol (30 ml) and tetrahydrofuran(8 ml) was allowed to stand at room temperature overnight. Triethylamine(0.5 ml) was added thereto and the mixture was concentrated. The residueobtained was purified by silica gel column chromatography (eluent; ethylacetate:hexane=1:5) to give the subject compound (1.78 g) as whitecrystals.

melting point=34°-36° C.

Rf value: 0.24 (ethyl acetate:hexane=1:5)

¹ H-NMR (CDCl₃ /TMS) δ: 1.28 & 1.57 (23H, 2br.s), 2.62 (2H, t, J=7.5Hz), 3.65 (2H, t, J=6 Hz), 7.23 (5H, m)

IR(KBr): 3344, 3259, 2918, 2848, 1468 cm⁻¹

MS(EI): 276 (M⁺)

(6) 13-Phenyltridecylmethanesulfonate

Triethylamine (1.2 ml) was added to a solution of the above-mentionedcompound (1.73 g) in dichloromethane (30 ml) and the mixture was cooledwith ice. Methanesulfonyl chloride (0.58 ml) was dropwise added theretoand the mixture was stirred at room temperature for 2 hours. Thereaction mixture was poured into ice water and extracted withdichloromethane. The dichloromethane layer was washed with a saturatedpotassium hydrogencarbonate solution, a 1% aqueous hydrochloric acidsolution and saturated brine and dried over magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:5) togive the subject compound (2.12 g) as white crystals.

melting point=45°-47° C.

Rf value: 0.39 (ethyl acetate:hexane=1:1)

¹ H-NMR (CDCl₃ /TMS) δ: 1.28 & 1.70 (22H, 2m), 2.62 (2H, t, J=7.8 Hz),3.01 (3H, s), 4.23 (2H, t, J=6 Hz), 7.22 (5H, m)

IR(KBr): 2920, 2851, 1474, 1344 cm⁻¹

MS(EI): 354 (M⁺)

elemental analysis: calculated C 67.75, H 9.67 found C 67.70, H 9.48

(7) 13-Phenyltridecyl iodide

Sodium iodide (1.165 g) was added to a solution of the above-mentionedcompound (2.12 g) in 2-butanone (60 ml) and the mixture was refluxedunder heating for 2 hours. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over magnesium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:9) to give thesubject compound (2.19 g) as white crystals.

melting point=19°-22° C.

Rf value: 0.88 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.27 & 1.70 (22H, 2m), 2.61 (2H, t, J=7.5 Hz),3.19 (2H, t, J=6.8 Hz), 7.21 (5H, m)

IR(KBr): 2917, 2851, 1472 cm⁻¹

MS(EI): 386 (M⁺)

elemental analysis: calculated C 75.63, H 9.91 found C 75.22, H 9.92

(8) Diethyl 2-acetamido-2-(13-phenyltridecyl)malonate

A solution of sodium ethoxide (0.764 g) in absolute ethanol (22 ml) wasdropwise added to diethyl acetamidomalonate (2.38 g) in a stream ofnitrogen and the mixture was stirred at 65° C. for 30 minutes. Asolution of the above-mentioned compound (2.11 g) in tetrahydrofuran (5ml) was dropwise added thereto and the mixture was stirred at 65° C. for6 hours. The reaction mixture was concentrated, poured into ice waterand extracted with ethyl acetate. The ethyl acetate layer was washedwith saturated brine and dried over anhydrous magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:3) togive the subject compound (2.06 g) as a colorless, oily substance.

Rf value: 0.41 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.25 (20H, m), 1.58 (2H, m), 2.02 (3H, s), 2.30(2H, m), 2.61 (2H, t, J=7.5 Hz), 4.23 (4H, q, J=6 Hz), 6.76 (1H, br.s),7.21 (5H, m)

IR(Neat): 3416, 3312, 2925, 2854, 1741, 1671 cm⁻¹

MS(EI): 475 (M⁺)

(9) 2-Acetamido-1,3-diacetoxy-2-(13-phenyltridecyl)propane

A solution (20 ml) of the above-mentioned compound (1.90 g) in anhydroustetrahydrofuran was added dropwise to a solution (40 ml) of lithiumaluminum hydride (0.56 g) in anhydrous tetrahydrofuran under ice-coolingin a stream of nitrogen and the mixture was stirred at room temperaturefor 2 hours. A saturated aqueous sodium sulfate solution was added tothe reaction mixture under ice-cooling and aluminum hydroxide producedwas filtered off. The solvent was distilled away and pyridine (8 ml) wasadded to the residue. Acetic anhydride (5 ml) was added thereto underice-cooling and the mixture was allowed to stand at room temperatureovernight. The reaction mixture was poured into 5% hydrochloric acidunder ice-cooling and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue obtained waspurified by silica gel column chromatography (eluent; ethyl acetate) togive the subject compound (1.01 g) as white crystals.

melting point=42°-45° C.

Rf value: 0.24 (ethyl acetate:hexane=1:1)

¹ H-NMR (CDCl₃ /TMS) δ: 1.26 & 1.61 (22H, 2m), 1.96 (3H, s), 2.08 (6H,s), 2.62 (2H, t, J=7.5 Hz), 4.30 (4H, s), 5.61 (1H, br.s), 7.21 (5H, m)

IR(KBr): 3295, 2926, 2854, 1748, 1660, 1553 cm⁻¹

MS(EI): 475 (M⁺)

elemental analysis: calculated C 70.70, H 9.54, N 2.94 found C 70.96, H9.52, N 2.96

(10) 2-Amino-2-(13-phenyltridecyl)-1,3-propanediol 1/4 hydrate

An aqueous solution (11.5 ml) of lithium hydroxide (0.88 g) was added toa solution of the above-mentioned compound (0.90 g) in methanol (11.5ml) and the mixture was refluxed under heating for 3 hours. The reactionmixture was concentrated and extracted with ethyl acetate. The ethylacetate layer was washed with saturated brine and dried over anhydrousmagnesium sulfate. The solvent was distilled away and the residue wasrecrystallized from ethyl acetate to give the subject compound (170 mg)as white crystals.

melting point=61°-64° C.

¹ H-NMR (CDCl₃ /TMS) δ: 1.27 & 1.60 (24H, 2m), 2.00 (4H, m), 2.62 (2H,t, J=7.5 Hz), 3.50 (4H, m), 7.22 (5H, m)

IR(KBr): 3342, 3290, 3157, 2916, 2849, 1581, 1472 cm⁻¹

MS(EI): 349 (M⁺)

elemental analysis: calculated C 74.63, H 11.24, N 3.96 found C 74.88, H10.94, N 3.92

EXAMPLE 288 2-Amino-2-{2-4-(6-phenylhexyloxy)phenyl!ethyl}-1,3-propanediol

(1) 6-Phenylhexylmethanesulfonate

Triethylamine (5.09 ml) was added to a solution of 6-phenylhexanol (5.0g) in dichloromethane (140 ml) and the mixture was cooled with ice.Methanesulfonyl chloride (2.50 ml) was dropwise added thereto and themixture was stirred at room temperature for 2 hours. The reactionmixture was poured into ice water and extracted with chloroform. Thechloroform layer was washed with a saturated potassium hydrogencarbonatesolution, a 1% aqueous hydrochloric acid solution and saturated brineand dried over magnesium sulfate. The solvent was distilled away and theresidue obtained was purified by silica gel column chromatography(eluent; ethyl acetate:hexane=1:2) to give the subject compound (8.08 g)as a colorless, oily substance.

Rf value: 0.45 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.15-1.95 (8H, m), 2.65 (2H, t, J=7.5 Hz), 2.99(3H, s), 4.22 (2H, t, J=6 Hz), 7.22 (5H, m)

IR(neat): 3027, 2937, 2858, 1497cm⁻¹

(2) 6-Phenylhexyl iodide

Sodium iodide (5.33 g) was added to a solution of the above-mentionedcompound (7.93 g) in 2-butanone (150 ml) and the mixture was refluxedunder heating for 2 hours. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over magnesium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:19) to give thesubject compound (7.62 g) as a colorless, oily substance.

Rf value: 0.78 (ethyl acetate:hexane=1:5)

¹ H-NHR (CDCl₃ /TMS) δ: 1.20-2.00 (8H, m), 2.60 (2H, t, J=7.5 Hz), 3.17(2H, t, J=6.5 Hz), 7.15 (5H, m)

IR(neat): 3026, 2930, 2855, 1496, 1453 cm⁻¹

MS(EI): 288 (M⁺)

(3) 2- 4-(6-Phenylhexyloxy)phenyl!ethanol

2-(4-Hydroxyphenyl)ethanol (3.97 g) and sodium ethoxide (2.30 g) wereadded to ethanol (130 ml) and the mixture was refluxed under heating for30 minutes. A solution of the above-mentioned compound (7.53 g) intetrahydrofuran (30 ml) was dropwise added thereto and the mixture wasstirred under reflux under heating for 6 hours. The reaction mixture wasconcentrated, poured into ice water and extracted with ethyl acetate.The ethyl acetate layer was washed with saturated brine and dried overmagnesium sulfate. The solvent was distilled away and the residueobtained was purified by silica gel column chromatography (eluent; ethylacetate:hexane=1:3) to give the subject compound (5.49 g) as acolorless, oily substance.

Rf value: 0.50 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.24-1.89 (8H, m), 2.59 (2H, t, J=7.5 Hz), 2.76(2H, t, J=5 Hz), 3.76 (2H, t, J=6.5 Hz), 3.89 (2H, t, J=5 Hz), 6.76 (2H,d, J=8.5 Hz), 7.06 (2H, d, J=8.5 Hz), 7.13 (5H, m)

IR(neat): 3355, 2933, 2858, 1613, 1512 cm⁻¹

MS(EI): 298 (M⁺)

(4) 2- 4-(6-Phenylhexyloxy)phenyl!ethylmethanesulfonate

Triethylamine (3.3 ml) was added to a solution of the above-mentionedcompound (5.40 g) in dichloromethane (100 ml) and the mixture was cooledwith ice. Methanesulfonyl chloride (1.7 ml) was dropwise added theretoand the mixture was stirred at room temperature for 2 hours. Thereaction mixture was poured into ice water and extracted withdichloromethane. The dichloromethane layer was washed with a saturatedpotassium hydrogencarbonate solution, a 1% aqueous hydrochloric acidsolution and saturated brine and dried over magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:2) togive the subject compound (6.99 g) as a colorless, oily substance.

Rf value: 0.39 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.30-1.92 (8H, m), 2.75 (2H, t, J=7.5 Hz), 2.81(3H, s), 2.96 (2H, t, J=7 Hz), 3.89 (2H, t, J=6 Hz), 4.33 (2H, t, J=7Hz), 6.80 (2H, d, J=8.5 Hz), 7.06 (2H, d, J=8.5 Hz), 7.15 (5H, m)

IR(neat): 2936, 2858, 1513 cm⁻¹

MS(EI): 376 (M⁺)

(5) 2- 4-(6-Phenylhexyloxy)phenyl!ethyl iodide

Sodium iodide (3.29 g) was added to a solution of the above-mentionedcompound (6.88 g) in 2-butanone (180 ml) and the mixture was refluxedunder heating for 4 hours. The reaction mixture was concentrated andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over magnesium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:9) to give thesubject compound (6.25 g) as a colorless, oily substance.

Rf value: 0.81 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.18-1.92 (8H, m), 2.60 (2H, t, J=7.5 Hz), 3.18(4H, m), 3.90 (2H, t, J=6 Hz), 6.75 (2H, d, J=8.5 Hz), 7.06 (2H, d,J=8.8 Hz), 7.10 (5H, m)

IR(neat): 2932, 2856, 1611, 1511 cm⁻¹

MS(EI): 408 (M⁺)

elemental analysis: calculated C 58.83, H 6.17 found C 58.88, H 6.53

(6) Diethyl 2-acetamido-2-{2- 4-(6-phenylhexyl)phenyl!ethyl}malonate

A solution of sodium ethoxide (3.20 g) in absolute ethanol (40 ml) wasdropwise added to diethyl acetamidomalonate (9.89 g) in a stream ofnitrogen and the mixture was stirred at 65° C. for 30 minutes. Asolution of the above-mentioned compound (6.20 g) in tetrahydrofuran (15ml) was dropwise added thereto and the mixture was stirred at 65° C. for6 hours. The reaction mixture was concentrated, poured into ice waterand extracted with ethyl acetate. The ethyl acetate layer was washedwith saturated brine and dried over anhydrous magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:3) togive the subject compound (4.04 g) as white crystals.

melting point=53°-55° C.

Rf Value: 0.18 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 1.84 (6H, t, J=7 Hz), 1.11-1.88 (10H, m), 1.97(3H, s), 2.24-2.76(6H, m), 3.87 (2H, t, J=6 Hz), 4.16 (4H, q, J=7 Hz),6.70 (1H, s), 6.74 (2H, d, J=8.5 Hz), 6.97 (2H, d, J=8.5 Hz), 7.15 (5H,m)

IR(neat): 3233, 2933, 1747, 1639, 1511 cm⁻¹

MS(EI): 497 (M⁺)

elemental analysis: calculated C 70.00, H 7.90, N 2.81 found C 69.83, H7.91, N 2.90

(7) 2-Acetamido-1,3-diacetoxy-2-{2-4-(6-phenylhexyloxy)phenyl!ethyl}propane

A solution (10 ml) of the above-mentioned compound (3.79 g) in anhydroustetrahydrofuran was dropwise added to a solution (60 ml) of lithiumaluminum hydride (0.87 g) in anhydrous tetrahydrofuran under ice-coolingin a stream of nitrogen and the mixture was stirred at room temperaturefor 2 hours. A saturated aqueous sodium sulfate solution was addedthereto under ice-cooling and aluminum hydroxide produced was filteredoff. The solvent was distilled away and pyridine (15 ml) was added tothe residue. Acetic anhydride (10 ml) was added thereto underice-cooling and the mixture was allowed to stand at room temperatureovernight. The reaction mixture was poured into ice-cooled 5%hydrochloric acid and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue obtained waspurified by silica gel column chromatography (eluent; ethyl acetate) togive the subject compound (1.80 g) as white crystals.

melting point=68°-70° C.

Rf value: 0.66 (ethyl acetate)

¹ H-NMR (CDCl₃ /TMS) δ: 1.24-1.88 (8H, m), 1.94 (3H, s), 2.06 (6H, s),2.10 (2H, m), 2.56 (4H, m), 3.88 (2H, t, J=7 Hz), 4.30 (4H, s), 5.60(1H, s), 6.72 (2H, d, J=8.5 Hz), 7.02 (2H, d, J=8.5 Hz), 7.13 (5H, m)

IR(KBr): 3319, 2934, 1739, 1652 cm⁻¹

MS(EI): 497 (M⁺)

elemental analysis: calculated C 70.00, H 7.90, N 2.81 found C 70.34, H7.93, N 2.86

(8) 2-Amino-2-{2- 4-(6-phenylhexyloxy)phenyl!ethyl)-1,3-propanediolhydrochloride

An aqueous solution (17 ml) of lithium hydroxide (1.33 g) was added to asolution of the above-mentioned compound (1.75 g) in methanol (25 ml)and the mixture was refluxed under heating for 3 hours. The reactionmixture was concentrated and extracted with ethyl acetate. The ethylacetate layer was washed with saturated brine and dried over anhydrousmagnesium sulfate. The solvent was distilled away and the residueobtained was recrystallized from ethyl acetate. A solution (10 ml) of 1Mhydrochloric acid in ether was added to a solution of the resultantcrystals in methanol (10 ml). The solvent was distilled away and thecrystals precipitated were recrystallized from ethyl acetate to give thesubject compound (0.90 g) as white crystals.

melting point=89°-91° C.

Rf value: 0.41 (chloroform:methanol:acetic acid:water 70:20:6:4)

¹ H-NMR (CDCl₃) δ: 1.33 (4H, m), 1.59 (6H, m), 1.91 (1H, br.s), 2.36(1H, br.s), 2.55 (2H, t, J=7.8 Hz), 3.72 (4H, m), 4.98 (1H, br.s), 6.66(2H, d, J=8.8 Hz), 7.03 (2H, d, J=8.8 Hz), 7.12 (3H, m), 7.22 (2H, m),7.85 (1H, br.s)

IR(KBr): 3275, 3028, 2934, 2858, 1513 cm⁻¹

MS(EI): 371 (M⁺)

elemental analysis: calculated C 67.71, H 8.40, N 3.43 found C 67.61, H8.30, N 3.42

EXAMPLE 289 2-Amino-2- 2-(4-undecyloxyphenyl)ethyl!-1,3-propanediol

(1) 2-(4-Undecyloxyphenyl)ethanol

A solution (300 ml) of 2-(4-hydroxyphenyl)ethanol (15.5 g), undecylbromide (25 ml) and sodium ethoxide (8.40 g) in ethanol was refluxedunder heating for 5 hours. The solvent was distilled away and water (200ml) and ethyl acetate (200 ml) were added thereto. The aqueous layer wasextracted with ethyl acetate (200 ml). The combined extract was driedand filtered. The solvent was distilled away and the residue obtainedwas purified by silica gel column chromatography (eluent; ethylacetate:hexane=1:3) to give 23.37 g of the subject compound as whitecrystals.

melting point=47°-50° C.

Rf value: 0.40 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=7.5 Hz), 1.10-1.58 (16H, m), 1.87 (2H,m), 2.78 (2H, t, J=7.5 Hz), 3.78 (2H, t, J=7 Hz), 3.89 (2H, t, J=7 Hz),6.82 (2H, d, J=9 Hz), 7.09 (2H, d, J=9 Hz)

IR(KBr): 3250, 2919, 2850, 1513, 1251 cm⁻¹

MS(EI): 292(M⁺)

(2) 2-(4-Undecyloxyphenyl)ethyl methanesulfonate

To a solution (400 ml) of the compound obtained above (23.24 g) indichloromethane was added triethylamine (14.4 ml). Methanesulfonylchloride (7.1 ml) was added to the mixture under ice-cooling and themixture was stirred at room temperature for 2 hours. Then, the reactionmixture was poured into 200 ml of ice water and extracted twice withdichloromethane (200 ml). The extract was dried and concentrated, andthe residue obtained was purified by silica gel column chromatography(eluent; ethyl acetate:hexane=1:3) to give the subject compound (28.07g) as white crystals.

melting point: 43°-44° C.

Rf value: 0.51 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 0.88 (3H, t, J=7.5 Hz), 1.25 (16H, m), 1.75 (2H,m), 2.81 (3H, s), 2.96 (2H, t, J=7 Hz), 3.90 (2H, t, J=6 Hz), 4.35 (2H,t, J=7 Hz), 6.75 (2H, d, J=9 Hz), 7.05 (2H, d, J=9 Hz)

IR(KBr): 2919, 2851, 1515, 1352 cm⁻¹

MS(EI): 370(M⁺)

elemental analysis: calculated C 64.83, H 9.25 found C 64.78, H 9.17

(3) 2-(4-Undecyloxyphenyl)ethyl iodide

A solution (350 ml) of the compound obtained above (27.95 g) and sodiumiodide (13.00 g) in 2-butanone was refluxed under heating for 3 hours.The solvent was distilled away and water (200 ml) was added thereto. Themixture was extracted twice with ethyl acetate (200 ml) and dried. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:19) togive the subject compound (26.45 g) as white crystals.

melting point=22°-23° C.

Rf value: 0.79 (ethyl acetate:hexane=1:5)

¹ H-NMR (CDCl₃ /TMS) δ: 0.88 (3H, t, J=7 Hz), 1.30 (16H, m), 1.75 (2H,m), 2.90-3.40 (4H, m), 3.90 (2H, t, J=7 Hz), 6.76 (2H, d, J=9 Hz), 7.02(2H, d, J=9 Hz),

IR(KBr): 2920, 2852, 1609, 1509, 1247 cm⁻¹

MS(EI): 402(M⁺)

(4) Diethyl 2-acetamido-2- 2-(4-undecyloxyphenyl)ethyl!malonate

A solution of sodium ethoxide (13.37 g) in absolute ethanol (400 ml) wasdropwise added to diethyl acetamidomalonate (42.68 g) in a stream ofnitrogen and the mixture was stirred at 65° C. for 30 minutes. Asolution of the compound obtained above (26.35 g) in tetrahydrofuran (50ml) was dropwise added thereto and the mixture was stirred at 65° C. for6 hours. The reaction mixture was concentrated, poured into ice waterand extracted with ethyl acetate. The ethyl acetate layer was washedwith saturated brine and dried over anhydrous magnesium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:5) togive the subject compound (13.94 g).

melting point=63°-65° C.

Rf value: 0.24 (ethyl acetate:hexane=1:2)

¹ H-NMR (CDCl₃ /TMS) δ: 0.86 (3H, t, J=7.1 Hz), 1.24 (20H, m), 1.41 (2H,m), 1.73 (2H, m), 1.97 (3H, s), 2.39 (2H, m), 2.62 (2H, m), 3.89 (2H, t,J=6.3 Hz), 4.18 (4H, m), 6.74 (1H, s), 6.77 (2H, d, J=8.3 Hz), 7.02 (2H,d, J=8.3 Hz)

IR(KBr): 3286, 2917, 2851, 1746, 1647, 1513 cm⁻¹

MS(EI): 491(M⁺)

elemental analysis: calculated C 68.40, H 9.22, N 2.85 found C 68.15, H9.23, N 2.80

(5) 2-Acetamido-1,3-diacetoxy-2- 2-(4-undecyloxyphenyl)ethyl!propane

A solution (60 ml) of the compound obtained above (13.02 g) in anhydroustetrahydrofuran was dropwise added to a solution (200 ml) of lithiumaluminum hydride (3.0 g) in anhydrous tetrahydrofuran in a stream ofnitrogen under ice-cooling and the mixture was stirred at roomtemperature for 2 hours. A saturated aqueous sodium sulfate solution wasadded to the reaction mixture under ice-cooling and the resultantaluminum hydroxide was filtered off. The solvent was distilled away andpyridine (40 ml) was added to the residue. Thereto was added aceticanhydride (30 ml) under ice-cooling and the mixture was allowed to standat room temperature overnight. The reaction mixture was poured intoice-cooled 5% hydrochloric acid and extracted with ethyl acetate. Theethyl acetate layer was washed with saturated brine and dried overanhydrous magnesium sulfate. The solvent was distilled away and theresidue obtained was purified by silica gel column chromatography(eluent; ethyl acetate) to give the subject compound (7.18 g) as whitecrystals.

melting point=82°-85° C.

Rf value: 0.6 (ethyl acetate)

¹ H-NMR (CDCl₃ /TMS) δ: 0.86 (3H, t, J=6.4 Hz), 1.24 (14H, m), 1.41 (2H,m), 1.75 (2H, m), 1.94 (3H, s), 2.07 (6H, s), 2.14 (2H, m), 2.53 (2H,m), 3.89 (2H, t, J=6.6 Hz), 4.32 (4H, s), 5.62 (1H, s), 6.79 (2H, d,J=8.8 Hz), 7.06 (2H, d, J=8.8 Hz)

IR(KBr): 3314, 2918, 2851, 1737, 1653 cm⁻¹

MS(EI): 491 (M⁺)

elemental analysis: calculated C 68.40, H 9.22, N 2.85 found C 68.36, H9.19, N 2.85

(6) 2-Amino-2- 2-(4-undecyloxyphenyl)ethyl!-1,3-propanediolhydrochloride

To a solution of the compound obtained above (7.16 g) in methanol (70ml) was added an aqueous solution (70 ml) of lithium hydroxide (5.50 g)and the mixture was refluxed under heating for 3 hours. The reactionmixture was concentrated and extracted with ethyl acetate. The ethylacetate layer was washed with saturated brine and dried over anhydrousmagnesium sulfate. The solvent was distilled away and the residue wasrecrystallized from ethyl acetate. To a solution of the thus obtainedcrystals in tetrahydrofuran (20 ml)-methanol (20 ml), 1M hydrochloricacid in ether (30 ml) was added. The solvent was distilled away and theprecipitated crystals were recrystallized from ethyl acetate to give thesubject compound (1.90 g).

melting point=88°-91° C.

¹ H-NMR (CDCl₃ --CD₃ OD/TMS) δ: 0.80 (3H, t, J=6.9 Hz), 1.19 (14H, m),1.36 (2H, m), 1.68 (2H, m), 1.85 (2H, m), 2.53 (2H, m), 3.65 (4H, m),3.84 (2H, t, J=6.4 Hz), 6.74 (2H, d, J=8.3 Hz), 7.04 (2H, d, J=8.3 Hz)

IR(KBr): 3274, 2921, 2852, 1613, 1513, 1247 cm⁻¹

MS(EI): 365(M⁺)

elemental analysis: calculated C 65.73, H 10.03, N 3.48 found C 65.53, H9.82, N 3.42

EXAMPLE 290 2-Amino-2- 2-(4-dodecylphenyl)ethyl!-1,3-propanediol

(1) 2-(4-Dodecanoylphenyl)ethyl acetate

Aluminum chloride (48.2 g) was added to dichloroethane (400 ml) in astream of nitrogen and the mixture was stirred at room temperature.Then, phenethyl acetate (39.6 g) and undecanoyl chloride (52.7 g) weredropwise added thereto under ice-cooling and the mixture was stirred atroom temperature overnight. The reaction mixture was poured into icewater and extracted with diethyl ether. The ether layer was washed withsaturated brine and dried over anhydrous magnesium sulfate. The solventwas distilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:20) to give thesubject compound (34.5 g) as pale yellow crystals.

melting point=32°-33° C.

IR(neat)_(max) : 2921, 2852, 1738, 1686, 1240 cm⁻¹

(2) 2-(4-Dodecylphenyl)ethanol

To a solution (50 ml) of the compound obtained above (34.5 g) intrifluoroacetic acid was added triethylsilane (22.7 ml) underice-cooling and the mixture was stirred at room temperature for 3 hours.The solvent was distilled away and ice water was poured to the residue.A cold, saturated aqueous sodium hydrogencarbonate solution was slowlyadded to the mixture. The mixture was extracted with ethyl acetate, andthe ethyl acetate layer was washed and dried over magnesium sulfate. Thesolvent was distilled away and methanol (250 ml) was added to theresidue to give a methanol solution. To the solution was added sodiummethoxide (10.2 g) and the mixture was refluxed under heating for 4hours. The reaction mixture was concentrated and ice water was poured tothe residue. The mixture was extracted with ethyl acetate. The ethylacetate layer was washed with a 5% aqueous hydrochloric acid solutionand saturated brine and dried over anhydrous magnesium sulfate. Thesolvent was distilled away to give the subject compound (27.1 g) as anoily substance.

Rf: 0.21 (ethyl acetate:hexane=1:3)

(3) 2-(4-Dodecylphenyl)ethyl iodide

To a solution (500 ml) of the compound obtained above (27.1 g) indichloromethane was added triethylamine (14.4 ml) and the mixture wasstirred at room temperature for 3 hours. The reaction mixture was pouredinto ice water and the mixture was extracted with dichloromethane. Thedichloromethane layer was washed with a saturated aqueous potassiumhydrogencarbonate solution, a 1% aqueous hydrochloric acid solution andsaturated brine and dried over anhydrous magnesium sulfate. The solventwas distilled away and 2-butanone (500 ml) was added to the residue.Thereto was added sodium iodide (12.2 g) and the mixture was refluxedunder heating for 3 hours. The reaction mixture was poured into icewater ahd extracted with ethyl acetate. The ethyl acetate layer waswashed with saturated brine and dried over anhydrous magnesium sulfate.The solvent was distilled away and the residue was purified by silicagel column chromatography (eluent; ethyl acetate:hexane=1:20) to givethe subject compound (18.6 g) as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.37 (3H, t, J=6 Hz), 0.66-0.86 (18H, m), 1.05-1.10(2H, m), 2.06(2H, t, J=6 Hz), 2.63 (2H, t, J=4 Hz), 2.83 (2H, t, J=4Hz), 6.60 (4H, dd, J=4 Hz, 8 Hz)

IR(neat)_(max) : 2919, 1513, 1467, 1168 cm⁻¹

(4) Diethyl 2-acetamido-2- 2-(4-dodecylphenyl)ethyl!malonate

A solution (100 ml) of sodium ethoxide (6.3 g) in absolute ethanol wasdropwise added to diethyl acetamidomalonate (20.2 g) in a stream ofnitrogen and the mixture was stirred at 65° C. for 30 minutes. Then, asolution (50 ml) of the compound obtained above (18.6 g) in anhydroustetrahydrofuran was dropwise added thereto and the mixture wad stirredat 65° C. for 3 hours. The reaction mixture was concentrated, pouredinto ice water and extracted with ethyl acetate. The extract was washedwith saturated brine and dried over anhydrous magnesium sulfate. Thesolvent was distilled away and the residue was purified by silica gelcolumn chromatography (eluent; ethyl acetate:hexane=1:3) to give thesubject compound (8.9 g).

melting point=60°-62° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.24 (6H, t, J=6 Hz), 1.23-1.59(18H, m), 1.54-1.59 (2H, m), 1.97 (3H, s), 2.45 (3H, t, J=6 Hz), 2.54(3H, t, J=6 Hz), 2.67 (3H, t, J=6 Hz), 4.15-4.24 (4H, m), 6.75 (1H,br.s), 7.06 (4H, dd, J=6 Hz, 6 Hz)

IR(KBr)_(max) : 3253, 2920, 2850, 1747, 1644, 1517 cm⁻¹

(5) 2-Acetamido-1,3-diacetoxy-2- 2-(4-dodecylphenyl)ethyl!propane

A solution (50 ml) of the compound obtained above (8.9 g) in anhydroustetrahydrofuran was dropwise added to a solution (200 ml) of lithiumaluminum hydride (1.38 g) in anhydrous tetrahydrofuran in a stream ofnitrogen under ice-cooling, and the mixture was stirred at roomtemperature for 2 hours. A saturated aqueous sodium sulfate solution wasadded to the reaction mixture under ice-cooling and the resultantaluminum hydroxide was filtered off. The resultant mixture was driedover anhydrous sodium sulfate and the solvent was distilled away.Pyridine (28.7 ml) was added to the residue. Thereto was added aceticanhydride (18.5 ml) under ice-cooling and the mixture was allowed tostand at room temperature overnight. The reaction mixture was pouredinto ice-cooled 5% hydrochloric acid and extracted with ethyl acetate.The ethyl acetate layer was washed with saturated brine and dried overanhydrous magnesium sulfate. The solvent was distilled away and theresidue was purified by silica gel column chromatography (eluent; ethylacetate:hexane=1:2) to give the subject compound (2.5 g) as whitecrystals.

melting point=111°14 113° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.24-1.31 (18H, m), 1.53-1.58(4H, m), 1.95 (3H, s), 2.09 (6H, s), 2.56 (2H, t, J=6 Hz), 2.58 (2H, t,J=6 Hz), 4.35 (4H, s), 5.62 (1H, br.s), 7.09 (4H, s)

IR(KBr): 3309, 2918, 2850, 1738, 1651 cm⁻¹

(6) 2-Amino-2- 2-(4-dodecylphenyl)ethyl!-1,3-propanediol hydrochloride

An aqueous solution (25 ml) of lithium hydroxide (1.7 g) was added to asolution (25 ml) of the compound obtained above (2.5 g) in methanol andthe mixture was refluxed under heating for 3 hours. The reaction mixturewas concentrated and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and a 26% hydrochloricacid-ethanol solution was added thereto, followed by stirring. Thesolvent was distilled away and the residue was recrystallized fromethanol to give the subject compound (770 mg) as white crystals.

¹ H-NMR (DMSO) δ: 0.88 (3H, t, J=6 Hz), 1.25-1.30 (18H, m), 1.52-1.58(2H, m), 1.94-2.02 (2H, m), 2.56-2.60 (2H, m), 2.64-2.68 (2H, m), 3.81(4H, dd, J=11, 26 Hz), 4.79 (2H, br.s), 7.09 (4H, dd, J=6, 26 Hz), 8.07(3H, br.s)

IR(KBr): 2921, 2852, 1738, 1686, 1250 cm⁻¹

EXAMPLE 291 2-Amino-2- 2-(2-octylphenyl)ethyl!-1,3-propanediol

(1) 1-(2-Bromophenyl)octanol

Magnesium pieces (6.56 g) were added to anhydrous tetrahydrofuran (10ml) in a stream of nitrogen and the mixture was stirred at roomtemperature. A solution (200 ml) of 1-bromoheptane (48.4 g) in anhydroustetrahydrofuran was dropwise added thereto while heating gradually andthe mixture was stirred at 40° C. for 1 hour. Thereto was dropwise addeda solution (100 ml) of 2-bromobenzaldehyde (25 g) in anhydroustetrahydrofuran at room temperature and the mixture was stirred for 1hour. The reaction mixture was poured into a saturated, aqueous ammoniumchloride solution and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:8) togive the subject compound (18.9 g) as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=6 Hz), 1.24-1.58 (10H, m), 1.61-1.79(2H, m), 5.05(1H, m, J=4 Hz), 7.08-7.12 (1H, m, J=6 Hz), 7.29-7.31 (1H,m, J=6 Hz), 7.50-7.54 (2H, m, J=4 Hz)

IR ν (neat): 3350, 2927, 1466, 1023 cm⁻¹

(2) trans-2-(1-Octenyl)bromobenzene

Diphosphorus pentaoxide (7.1 g) was added to a solution (200 ml) of thecompound obtained above (2.85 g) in benzene and the mixture was refluxedunder heating for 2 hours. The diphosphorus pentaoxide was filtered offand the solvent was distilled away. Ice water was added to the residue.The mixture was extracted with ethyl acetate, and the ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:15) togive the subject compound (2.4 g) as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=7 Hz), 1.18-1.45 (6H, m), 1.46-1.55(2H, m), 2.24 (2H, m, J=1 Hz, 7 Hz), 6.16 (1H, m, J=7 Hz), 6.72 (1H, d,J=16 Hz), 7.02-7.08 (1H, m), 7.19-7.33 (1H, m), 7.46-7.55 (2H, m)

IR ν (neat): 2957, 2855, 1466, 1023cm⁻¹

(3) trans-2-(1-Octenyl)-benzaldehyde

Magnesium pieces (3.74 g) were added to anhydrous tetrahydrofuran (10ml) in a stream of nitrogen and the mixture was stirred at roomtemperature. A solution (100 ml) of the compound obtained above (37.4 g)in anhydrous tetrahydrofuran was dropwise added thereto while heatinggradually and the reaction mixture was stirred at 60° C. for 1.5 hours.Thereto was dropwise added a solution (100 ml) of dimethylformamide(11.5 ml) in anhydrous tetrahydrofuran at room temperature and themixture was stirred overnight. The reaction mixture was poured into asaturated aqueous ammonium chloride solution and extracted with ethylacetate. The ethyl acetate layer was washed with saturated brine anddried over anhydrous magnesium sulfate. The solvent was distilled awayand the residue was purified by silica gel column chromatography(eluent; ethyl acetate:hexane=1:15) to give the subject compound (26.7g) as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6 Hz), 1.22-1.38 (6H, m), 1.45-1.52(2H, m), 2.24-2.36 (2H, m), 6.11-6.18 (1H, m), 7.15 (1H, d, J=18 Hz),7.33-7.37 (1H, m), 7.48-7.53 (2H, m), 7.58 (1H, d, J=4 Hz), 10.31 (1H,s)

IRν (neat): 2927, 2855, 1699, 1597 cm⁻¹

(4) 2-Octylbenzaldehyde

To a solution (200 ml) of the compound obtained above (26.7 g) inmethanol was added a solution (20 ml) of 10% palladium carbon (1 g) inmethanol and the mixture was stirred at ordinary temperature and atatmospheric pressure in a stream of hydrogen for 14 hours for catalyticreduction. The 10% palladium carbon was filtered off and the solvent wasdistilled away. The residue was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:20) to give the subjectcompound (22 g) as an oil.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=7 Hz), 1.25-1.38 (10H, m), 1.54-1.63(2H, m), 3.00 (2H, t, J=7 Hz), 7.24-7.26 (1H, m), 7.31-7.35 (1H, m),7.46-7.50 (1H, m), 7.80-7.83 (1H, m), 10.28 (1H, s)

IR ν (neat): 3335, 2926, 1701, 1601cm⁻¹

(5) Ethyl (2-octylphenyl)acetate

Methyl methylsulfinylmethyl sulfide (12.4 g) and Triton B (9.16 ml) wereadded to a solution (100 ml) of the compound obtained above (22 g) indioxane at room temperature and the mixture was refluxed under heatingfor 2 hours. The solvent was distilled away and ethyl acetate was addedto the residue. The ethyl acetate layer was washed with saturated brineand dried over anhydrous magnesium sulfate. The solvent was distilledaway and ethanol (200 ml) was added to the residue Thereto was added a26% hydrochloric acid-ethanol solution and the mixture was stirred atroom temperature for 30 minutes. The solvent was distilled away and icewater was poured to the residue. The mixture was extracted with ethylacetate. The extract was washed with saturated brine and dried overanhydrous magnesium sulfate. The solvent was distilled away and theresidue was purified by silica gel column chromatography (eluent; ethylacetate:hexane=1:30) to give the subject compound (20.2 g) as an oilysubstance.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=5 Hz), 1.19-1.38 (10H, m), 1.24 (3H,t, J=5 Hz), 1.49-1.62 (2H, m), 2.59 (2H, t, J=6 Hz), 3.85 (2H, s), 4.13(2H, q, J=5 Hz), 7.10-7.35 (4H, m)

(6) 2-(2-Octylphenyl)ethyl alcohol

A solution (50 ml) of the compound obtained above (20.2 g) in anhydroustetrahydrofuran was dropwise added to a solution (200 ml) of lithiumaluminum hydride (3.04 g) in anhydrous tetrahydrofuran in stream ofnitrogen under ice-cooling and the mixture was stirred at roomtemperature for 2 hours. A saturated aqueous sodium sulfate solution wasadded to the reaction mixture under ice-cooling and the resultantaluminum hydroxide was filtered off. The filtrate was dried overanhydrous sodium sulfate and the solvent was distilled away. The residuewas purified by silica gel column chromatography (eluent; ethylacetate:hexane=1:30) to give the subject compound (10.2 g) as an oilysubstance.

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6 Hz), 1.21-1.46 (10H, m), 1.47-1.62(2H, m), 2.61(2H, t, J=6 Hz), 2.96 (3H, t, J=6 Hz), 3.82 (2H, dd, J=6Hz, 12 Hz), 7.14-7.24 (4H, m)

IR ν (neat): 3335, 2926, 2854, 1467cm⁻¹

(7) 2-(2-Octylphenyl)ethyl methanesulfonate

Triethylamine (7.37 ml) was added to a solution (250 ml) of the compoundobtained above (10.2 g) in dichloromethane and the mixture was cooledwith ice. Thereto was dropwise added methanesulfonyl chloride (6.04 g)and the mixture was stirred at room temperature for 2 hours. Thereaction mixture was poured into ice water and extracted withdichloromethane. The dichloromethane layer was washed with a saturatedaqueous potassium hydrogencarbonate solution, a 1% aqueous hydrochloricacid solution and saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:8) gogive the subject compound (13.4 g) as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.22-1.41 (10H, m), 1.51-1.59(2H, m), 2.60 (2H, t, J=6 Hz), 2.84 (3H, 3.09 (2H, t, J=6 Hz), 4.38 (2H,t, J=6 Hz), 7.10-7.20 (4H, m)

IR(neat): 2929, 1467, 1357, 1174 cm⁻¹

(8) 2-(2-Octylphenyl)ethyl iodide

To a solution of the compound obtained above (13.4 g) in 2-butanone (300ml) was added sodium iodide (7.7 g) and the mixture was refluxed underheating for 2 hours. The reaction mixture was poured into ice water andextracted with ethyl acetate. The ethyl acetate layer was washed withsaturated brine and dried over anhydrous magnesium sulfate. The solventwas distilled away and the residue was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:30) to give the subjectcompound (11.9 g).

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6 Hz), 1.18-1.74 (10H, m), 1.50-1.59(2H, m), 2.57 (2H, t, J=6 Hz), 3.18 (2H, t, J=6 Hz), 3.28 (2H, t, J=6Hz), 7.10-7.25 (4H, m)

IR(neat): 2923, 2854, 1490, 1468 cm⁻¹

(9) Diethyl 2-acetamido-2- 2-(2-octylphenyl)ethyl!malonate

A solution (50 ml) of sodium ethoxide (6.39 g) in anhydrous ethanol wasdropwise added to diethyl acetamidomalonate (20.4 g) in a stream ofnitrogen and the mixture was stirred at 65° C. for 1.5 hours. A solutionof the compound obtained above (10.8 g) in tetrahydrofuran was dropwiseadded thereto and the mixture was refluxed under heating for 7 hours.The reaction mixture was concentrated, poured into ice water andextracted with ethyl acetate. The extract was washed with saturatedbrine and dried over anhydrous magnesium sulfate. The solvent wasdistilled away and the residue was purified by silica gel columnchromatography (eluent; ethyl acetate:hexane=1:3) to give the subjectcompound (5.8 g) as white crystals.

melting point=37°-38° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.21-1.36 (10H, m), 1.25 (6H,t, J=6 Hz), 1.46-1.57 (2H, m), 2.03 (3H, s), 2.38-2.47 (2H, m), 2.51(2H, t, J=6 Hz), 2.55-2.63 (2H, m, J=6 Hz), 4.16-4.41 (4H, m), 6.82 (2H,br.s), 7.05-7.15 (4H, m)

IR(KBr): 3415, 2977, 2855, 1741, 1683, 1492 cm⁻¹

(10) 2-Acetamido-1,3-diacetoxy-2- 2-(2-octylphenyl)ethyl!propane

A solution (50 ml) of the compound obtained above (4.3 g) in anhydroustetrahydrofuran was dropwise added to a solution (200 ml) of lithiumaluminum hydride (0.76 g) in anhydrous tetrahydrofuran in a stream ofnitrogen under ice-cooling, and the mixture was stirred at roomtemperature for 2 hours. A saturated aqueous sodium sulfate solution wasadded to the reaction mixture under ice-cooling and the resultantaluminum hydroxide was filtered off. The filtrate was dried overanhydrous sodium sulfate and the solvent was distilled away. Pyridine(10 ml) was added to the residue and then, acetic anhydride (13 ml) wasadded thereto, and the mixture was allowed to stand at room temperatureovernight. The reaction mixture was poured into ice-cooled 5%hydrochloric acid and extracted with ethyl acetate. The ethyl acetatelayer was washed with saturated brine and dried over anhydrous magnesiumsulfate. The solvent was distilled away and the residue was purified bysilica gel column chromatography (eluent; ethyl acetate:hexane=1:3) togive the subject compound (2.2 g) as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6 Hz), 1.21-1.38 (12H, m), 1.47-1.58(2H, m), 1.97 (3H, s), 2.08 (6H, s), 2.56 (2H, t, J=6 Hz), 2.58 (2H, t,J=6 Hz), 4.35 (4H, s), 5.66 (1H, br.s), 7.09-7.13 (4H, m)

IR(neat): 3295, 2927, 1747, 1660, 1256 cm⁻¹

(11) 2-Amino-2- 2-(2-octylphenyl)ethyl!-1,3-propanediol hydrochloride

An aqueous solution (20 ml) of lithium hydroxide (1.7 g) was added to asolution of the compound obtained above (2.2 g) in methanol (20 ml) andthe mixture was refluxed under heating for 4 hours. The reaction mixturewas concentrated and extracted with ethyl acetate. The extract waswashed with saturated brine and dried over anhydrous magnesium sulfate;The solvent was distilled away and a 26% hydrochloric acid-ethanolsolution was added to the residue. The solvent was distilled away andthe residue was recrystallized from ethanol to give hydrochloride of thesubject compound (800 mg).

melting point=168°-170° C.

¹ H-NMR (DMSO) δ: 0.85 (3H, t, J=7 Hz), 1.22-1.37 (10H, m), 1.43-1.54(2H, m), 1.68-1.78 (2H, m), 2.52-2.63 (4H, m), 3.49-3.59 (4H, m), 5.40(2H, t, J=4 Hz), 7.05-7.17 (4H, 7.89 (3H, br.s)

IR ν (KBr): 3385, 3272, 2925, 1519, 1069 cm⁻¹

EXAMPLE 292 2-Amino-2-(4-octylthiobenzyl)-1,3-propanediol hydrochloride1/2 hydrate

(1) 4-(Methylthio)benzyl alcohol

Sodium borohydride (3.78 g) was added to isopropyl alcohol (50 ml) andthe mixture was stirred under ice-cooling. Thereto was dropwise added4-(methylthio)benzaldehyde (15 g) and the mixture was stirred at roomtemperature for 30 minutes. The solvent was distilled away and water wasadded to the residue. The mixture was extracted with ethyl acetate. Theorganic layer was washed with saturated brine and dried over anhydroussodium sulfate. The solvent was distilled away and the residue obtainedwas recrystallized from hexane-ethyl acetate to give the subjectcompound (15 g) as white crystals.

melting point=41°-43° C.

¹ H-NMR (CDCl₃) δ: 2.40 (3H, s), 4.43 (2H, s), 7.10 (4H, s), 3.36 (1H,br.s)

elemental analysis(C₈ H₁₀ OS): calculated C 62.30, H 6.54 found C 61.90,H 6.55

MS: 154 (M⁺)

(2) 4-(Methylsulfinyl)benzyl alcohol

m-Chloroperbenzoic acid (content 50%, 35 g) was added to a solution (100ml) of the compound obtained above (15 g) in chloroform underice-cooling and the mixture was stirred for 1 hour. Thereto was addedcalcium hydroxide (37 g) and the mixture was stirred at room temperaturefor 1 hour. The insoluble matters were filtered off, and the filtratewas washed with saturated brine and dried over anhydrous sodium sulfate.The solvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; chloroform:methanol=20:1) togive the subject compound (15.56 g) as an oily substance.

¹ H-NMR (CDCl₃) δ: 2.73 (3H, s), 3.28 (1H, br.s), 4.45 (2H, s), 7.52(4H, s)

IR(neat): 3364, 1409, 1303, 1148, 1031 cm⁻¹

elemental analysis(C₈ H₁₀ O₂ S): calculated C 56.45, H 5.92 found C56.51, H 5.87

MS: 170 (M⁺)

(3) 4-(Methylsulfinyl)benzyl methanesulfonate

Triethylamine (14 ml) was added to a solution (100 ml) of the compoundobtained above (13.88 g) in dichloromethane under ice-cooling. Theretowas dropwise added methanesulfonyl chloride (6.2 ml) and the mixture wasstirred for 30 minutes. The reaction mixture was poured into ice waterand extracted with dichloromethane. The organic layer was washed with asaturated aqueous sodium hydrogencarbonate solution, 0.1N hydrochloricacid and saturated brine and dried over anhydrous sodium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; chloroform:methanol=10:1) togive the subject compound (15.38 g) as white crystals.

melting point=63°-65° C.

¹ H-NMR (CDCl₃) δ: 2.74 (3H, s), 3.0 (3H, s), 5.22 (2H, s), 7.52 (2H, d,J=8 Hz), 7.63 (2H, d, J=8 Hz)

IR(KBr): 3015, 1349, 1172, 1040, 951 cm⁻¹

elemental analysis(C₉ H₁₂ O₄ S₂): calculated C 43.53, H 4.87 found C43.51, H 4.82

MS: 248 (M⁺)

(4) 4-(Methylsulfinyl)benzyl iodide

To a solution (100 ml) of the compound obtained above (8.25 g) in2-butanone was added sodium iodide (7.5 g) and the mixture was stirredat room temperature for 1 hour. The reaction mixture was concentrated,poured into ice water and extracted with ethyl acetate. The organiclayer was washed with saturated brine and dried over anhydrous sodiumsulfate. The solvent was distilled away and the residue was purified bysilica gel column chromatography (eluent; chloroform:methanol=10:1) togive the subject compound (8.65 g) as yellow crystals.

melting point=80°-81° C.

¹ H-NMR (CDCl₃) δ: 2.70 (3H, s), 4.42 (3H, s), 7.50 (4H, s)

IR(KBr): 1399, 1153, 1038, 837, 565 cm⁻¹

elemental analysis(C₈ H₉ OSI): calculated C 34.30, H 3.24 found C 34.17,H 3.21

MS: 280 (M⁺)

(5) Diethyl 2-acetamido-2-(4-methylsulfinylbenzyl)malonate

Sodium ethoxide (4 g) was added to a solution (200 ml) of diethylacetamidomalonate (13 g) in absolute ethanol in a stream of nitrogen andthe mixture was stirred at 65° C. for 1 hour. A solution of the compoundobtained above (8.4 g) in absolute ethanol was dropwise added theretoand the mixture was stirred at 65° C. for 1 hour. The reaction mixturewas concentrated, poured into ice water and extracted with ethylacetate. The extract was washed with saturated brine and dried overanhydrous sodium sulfate. The solvent was distilled away and the residuewas purified by silica gel column chromatography (eluent;chloroform:methanol=20:1) to give the subject compound (8.2 g) ascrystals.

melting point=135°-136° C.

¹ H-NMR (CDCl₃) δ: 1.28 (6H, t, J=7 Hz), 2.02 (3H, s), 2.70 (3H, s),3.70 (2H, s), 4.25 (4H, m), 6.52 (1H, s), 7.15 (2H, d, J=8 Hz), 1.53(2H, d, J=8 Hz)

IR(KBr): 3253, 2986, 1748, 1642, 1198, 1039 cm⁻¹

elemental analysis(C₁₇ H₂₃ NO₆ S): calculated C 55.27, H 6.27, N 3.79found C 55.09, H 6.25, N 3.78

(6) Diethyl 2-acetamido-2-(4-mercaptobenzyl)malonate

The compound obtained above (6.22 g) was added to trifluoroaceticanhydride (50 ml) under ice-cooling and the mixture was stirred for 1hour. The trifluoroacetic anhydride was removed, and ethanol (100 ml)and triethylamine (100 ml) were added thereto. The mixture was stirredat room temperature for 1 hour. The reaction mixture was concentratedand chloroform (200 ml) was added thereto. Then, the mixture was washedwith a saturated aqueous ammonium chloride solution and dried overanhydrous sodium sulfate. The solvent was distilled away and the residuewas purified by silica gel column chromatography (eluent;chloroform:methanol: 10:1) to give the subject compound (4.26 g) ascrystals.

melting point: 125°-128° C.

¹ H-NMR (CDCl₃) δ: 1.27 (6H, t, J=7 Hz), 2.00 (3H, s), 3.38 (1H, s),3.57 (2H, s), 4.24 (4H, m), 6.50 (1H, s), 6.85 (2H, d, J=8 Hz), 7.14(2H, d, J=8 Hz)

IR(KBr): 3398, 2986, 2547, 1736, 1665, 1212, 1018 cm⁻¹

elemental analysis(C₁₆ H₂₁ NO₅ S): calculated C 56.62, H 6.24, N 4.13found C 56.61, H 6.20, N 4.09

MS: 339 (M⁺)

(7) Diethyl 2-acetamido-2-(4-octylthiobenzyl)malonate

1-Bromooctane (0.58 g) and potassium carbonate (0.5 g) were added to asolution (10 ml) of the compound obtained above (1 g) indimethylformamide and the mixture was stirred at room temperature for 5hours. The reaction-mixture was poured into ice water and extracted withethyl acetate. The organic layer was washed with a saturated aqueousammonium chloride solution and dried over anhydrous sodium sulfate. Thesolvent was distilled away and the residue was purified by silica gelcolumn chromatography (eluent; chloroform:methanol=25:1) to give thesubjected compound (1.16 g) as crystals.

melting point=82°-84° C.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=7 Hz), 1.27 (14H, m), 1.40 (2H, quint,J=7 Hz), 1.61 (2H, quint, J=7 Hz), 2.01 (3H, s), 2.86 (2H, t, J=7 Hz),3.58 (2H, s),4.25 (4H, m), 6.51 (1H, s), 6.89 (2H, d, J=8 Hz), 7.17 (2H,d, J=8 Hz)

IR(KBr): 3255, 2952, 1747, 1644, 1298, 1274, 1220 cm⁻¹

elemental analysis(C₂₄ H₃₇ NO₅ S): calculated C 63.83, H 8.26, N 3.10found C 63.33, H 8.14, N 3.06

MS: 451 (M⁺)

(8) 2-Acetamido-2-(4-octylthiobenzyl)-1,3-propanediol

A solution (10 ml) of the compound obtained above (1 g) in anhydroustetrahydrofuran was dropwise added to a solution of lithium aluminumhydride (0.26 g) in anhydrous tetrahydrofuran (10 ml) under ice-cooling.The mixture was stirred under ice-cooling for 1 hour and at roomtemperature for 1 hour. Then, thereto was dropwise added a saturatedaqueous sodium sulfate solution to decompose the lithium aluminumhydride. The insoluble matters were filtered off and the filtrate wasextracted with ethyl acetate. The organic layer was washed withsaturated brine and dried over anhydrous sodium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; chloroform:methanol=10:1) to give thesubjected compound (0.6 g) as crystals.

melting point=76°-78° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=7 Hz), 1.25 (8H, m), 1.40 (2H, quint,J=7 Hz), 1.61 (2H, quint, J=7 Hz), 1.99 (3H, s), 2.87 (2H, t, J=7 Hz),2.89 (2H, s), 3.50 (2H, m), 3.70 (2H, m), 3.73 (2H, m, --OH×2), 5.79(1H, s, --NH), 7.14 (2H, d, J=8 Hz), 7.25 (2H, d, J=8 Hz)

IR(KBr): 3422, 3347, 3192, 2942, 1654, 1550, 1055 cm⁻¹

elemental analysis(C₂₀ H₃₃ NO₃ S): calculated C 65.36, H 9.05, N 3.81found C 65.29, H 9.11, N 3.75

MS: 367 (M⁺)

(9) 2-Amino-2-(4-octylthiobenzyl)-1,3-propanediol hydrochloride

An aqueous solution (5 ml) of lithium hydroxide (380 mg) was added to asolution (5ml) of the compound obtained above (400 mg) in methanol andthe mixture was refluxed under heating for 4 hours. The reaction mixturewas concentrated and extracted with ethyl acetate. The extract waswashed with saturated brine and dried over anhydrous sodium sulfate. Thesolvent was distilled away to give white powder. The thus-obtainedpowder was dissolved in ethanol (2 ml) and thereto was added a 26%hydrochloric acid-ethanol solution(1 ml). The solvent was distilled awayand the precipitated crystals were recrystallized from hexane-ethylacetate to give the subjected compound (80 mg).

melting point=100°-102° C.

¹ H-NMR (CD₃ OD) δ: 0.76 (3H, t, J=7 Hz), 1.16 (8H, m), 1.30 (2H, m),1.53 (2H, quint, J=7 Hz), 2.79 (2H, t, J=7 Hz), 2.86 (2H, s), 3.43 (2H,m), 3.62 (3H, m), 7.06 (2H, d, J=8 Hz), 7.15 (2H, d, J=8 Hz)

IR(KBr): 3363, 3286, 2924, 1516, 1494, 1072 cm⁻¹

elemental analysis(C₁₈ H₃₁ NO₂ S HCl 1/2H₂ O): calculated C 58.28, H8.97, N 3.78 found C 58.44, H 9.02, N 3.68

EXAMPLE 293 2-Amino-2- 2-(5-octyl-2-thienyl)ethyl!-1,3-propanediolhydrochloride

(1) 2-(2-Thienylethyl)-2-tetrahydropyranyl ether

To a solution (100 ml) of 2-(2-thienyl)ethanol (12.85 g) indichloromethane, 3,4-dihydro-2H-pyran (9.25 g) and p-toluenesulfonicacid (2 g) were added. The mixture was stirred at room temperature for 4hours. The solvent was distilled away and ethyl acetate was addedthereto. The mixture was washed with saturated brine and dried overanhydrous sodium sulfate. The solvent was distilled away and the oilysubstance obtained was purified by distillation to give 13.52 g of thesubject compound as an oily substance. boiling point=107°-108° C./1 mmHg

¹ H-NMR (CDCl₃) δ: 1.50 (4H, m), 1.70 (1H, m), 1.82 (1H, m), 3.11 (2H,t, J=7 Hz), 3.47 (1H, m), 3.60 (1H, dt, J=10, 7 Hz), 3.79 (1H, m), 3.95(1H, dt, J=10,7 Hz), 4.61 (1H, t, J=3.5 Hz), 6.83 (1H, dd, J=l, 3.4 Hz),6.90 (1H, dd, J=3.4, 5.4 Hz), 7.11 (1H, dd, J=l, 5.4 Hz)

IR(neat): 2930, 1250, 1120, 1030, 870 cm⁻¹

elemental analysis C₁₁ H₁₆ O₂ S: calculated C 62.23, H 7.60 found C62.83, H 7.01

MS: 212 (M⁺)

(2) 2-(5-Octyl-2-thienyl)ethyl 2-tetrahydropyranyl ether

A solution (100 ml) of the above-mentioned compound (8.5 g) in anhydroustetrahydrofuran was cooled to -78° C. and a solution (1.63 mol/l, 30 ml)of n-butyl lithium in hexane was dropwise added thereto. The mixture wasstirred under ice-cooling for 30 minutes and then at room temperaturefor 30 minutes. A solution (15 ml) of 1-bromooctane (10 g) in anhydroustetrahydrofuran was dropwise added thereto and the mixture was stirredat room temperature for 7 hours. The reaction mixture was poured intoice water and extracted with ethyl acetate. The organic layer was washedwith a saturated aqueous ammonium chloride solution and dried overanhydrous sodium sulfate. The solvent was distilled away and the residueobtained was purified by silica gel column chromatography (eluent;hexane:ethyl acetate=20:1) to give 6.6 g of the subject compound as anoily substance.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, 7 Hz), 1.25 (10H, m), 1.53 (4H, m), 1.62(2H, m), 1.72 (1H, m), 1.83 (1H, m), 2.71 (2H, t, J=7 Hz), 3.02 (2H, t,J=7 Hz), 3.46 (1H, m), 3.60 (1H, dr, J=10, 7 Hz), 3.80 (1H, m), 3.92(1H, dt, J=10, 7 Hz), 4.61 (1H, t, J=3.5 Hz), 6.54 (1H, d, J=3.4 Hz),6.61 (1H, d, J=3.4 Hz)

IR(neat): 2927, 2854, 1135, 1120, 1033 cm⁻¹

elemental analysis C₁₉ H₃₂ O₂ S: calculated C 70.32, H 9.94 found C70.12, H 10.03

MS: 324 (M⁺)

(3) 2-(5-Octyl-2-thienyl)ethanol

Tetrahydrofuran (20 ml) and p-toluenesulfonic acid (0.3 g) were added toa solution (80 ml) of the above-mentioned compound (6.5 g) in methanoland the mixture was stirred at room temperature for 1 hour. The solventwas distilled away and ethyl acetate was added to the resulting mixture.The mixture was washed with saturated brine and dried over anhydroussodium sulfate. The solvent was distilled away and the residue obtainedwas purified by silica gel column chromatography (eluent; hexane:ethylacetate=5:1) to give 4 g of the subject compound as an oil.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=7 Hz), 1.27 (10H, m), 1.62 (2H, quint,J=7 Hz), 2.73 (2H, t, J=7 Hz), 3.00 (2H, t, J=6 Hz), 3.80 (2H, t, J=6Hz), 6.58 (1H, d, J=3.4 Hz), 6.64 (1H, d, J=3.4 Hz)

IR(neat): 3348, 2927, 2854, 1466, 1047, 797 cm⁻¹

elemental analysis : calculated C 69.43, H 10.07 C₁₄ H₂₄ OS.0.1H₂ Ofound C 69.34, H 10.17

MS: 240 (M⁺)

(4) 2-(5-Octyl-2-thienyl)ethyl methanesulfonate

Triethylamine (3 ml) was added to a solution (50 ml) of theabove-mentioned compound (4 g) in dichloromethane. Methanesulfonylchloride (1.5 ml) was dropwise added thereto and the mixture was stirredfor 30 minutes. The reaction mixture was poured into ice water andextracted with dichloromethane. The organic layer was washed with asaturated aqueous sodium hydrogencarbonate solution, 0.1N hydrochloricacid and saturated brine, and dried over anhydrous sodium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; chloroform:methanol=20:1) togive 5 g of the subject compound as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=7 Hz), 1.27 (10H, m), 1.61 (2H, quint,J=7 Hz), 2.72 (2H, t, J=7.8 Hz), 2.91 (3H, s), 3.17 (2H, t, J=3.4 Hz),4.37 (2H, t, J=6.8 Hz), 6.58 (1H, d, J=3.4 Hz), 6.67 (1H, d, J=3.4 Hz)

IR(neat): 2927, 2854, 1357, 1176, 959, 802 cm⁻¹

elemental analysis C₁₅ H₂₆ O₃ S₂ : calculated C 56.57, H 8.23 found C56.19, H 8.10

MS: 318 (M⁺)

(5) 2-(5-Octyl-2-thienyl)ethyl iodide

Sodium iodide (4.5 g) was added to a solution (50 ml) of theabove-mentioned compound (4.8 g) in 2-butanone and the mixture wasstirred at room temperature for 17 hours. The reaction mixture wasconcentrated, poured into ice water and extracted with ethyl acetate.The organic layer was washed with saturated brine and dried overanhydrous sodium sulfate. The solvent was distilled away and the residuewas purified by silica gel column chromatography (eluent; hexane:ethylacetate =20:1) to give 4.9 g of the subject compound as an oilysubstance.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=7 Hz), 1.28 (10H, m), 1.62 (2H, quint,J=7 Hz), 2.72 (2H, t, J=7.5 Hz), 3.30 (4H, m), 6.57 (1H, d, J=3.4 Hz),6.63 (1H, d, J=3.4 Hz)

IR(neat): 2926, 2853, 1466, 1168, 796 cm⁻¹

elemental analysis C₁₄ H₂₃ SI: calculated C 48.00, H 6.62 found C 48.29,H 6.99

MS: 350 (M⁺)

(6) Diethyl 2-acetamido-2- 2-(5-octyl-2-thienyl)ethyl!malonate

60% Oily sodium hydride (0.33 g) was suspended in anhydrousdimethylformamide (20 ml) and diethyl acetamidomalonate (1.82 g) wasadded thereto. The mixture was stirred at room temperature for 1 hour.Then, a solution (10 ml) of the above-mentioned compound (2.7 g) inanhydrous dimethylformamide was dropwise added thereto and the mixturewas stirred at room temperature for 10 hours. The reaction mixture waspoured into ice water and extracted with ethyl acetate. The extract waswashed with a saturated aqueous ammonium chloride solution and driedover anhydrous sodium sulfate. The solvent was distilled away and theresidue was purified by silica gel column chromatography (eluent;hexane:ethyl acetate=2:1) to give 1.4 g of the subject compound ascrystals.

melting point=57°-58° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=7 Hz), 1.25 (16H, m), 1.57 (2H, quint,J=7 Hz), 2.0 (3H, s), 2.61 (2H, m), 2.70 (4H, m), 4.20 (4H, m), 6.52(1H, d, J=3.4 Hz), 6.53 (1H, d, J=3.4 Hz), 6.75 (1H, s)

IR(neat): 3278, 2923, 2852, 1746, 1647, 1211, 1195 cm⁻¹

elemental analysis : calculated C 62.84, H 8.48, N 3.19 C₂₃ H₃₇ NO₅ Sfound C 62.80, H 8.42, N 2.94

MS: 439 (M⁺)

(7) 2-Acetamido-2- 2-(5-octyl-2-thienyl)ethyl!-1,3-propanediol

A solution (15 ml) of the above-mentioned compound (1.3 g) in anhydroustetrahydrofuran was dropwise added to a solution (15 ml) of lithiumaluminum hydride (0.38 g) in anhydrous tetrahydrofuran underice-cooling. After stirring under ice-cooling for 1 hour, the mixturewas stirred at room temperature for 1 hour. A saturated aqueous sodiumsulfate solution was dropwise added under ice-cooling to decomposelithium aluminum hydride. The insoluble matters were filtered off andthe filtrate was extracted with ethyl acetate. The organic layer waswashed with saturated brine and dried over anhydrous sodium sulfate. Thesolvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; chloroform:methanol=15:1) togive 0.5 g of the subject compound as crystals.

melting point=58°-60° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=7 Hz), 1.27 (10H, m), 1.60 (2H, m),1.94 (3H, s), 2.02 (2H, m), 2.71 (2H, t, J=7 Hz), 2.82 (2H, t, J=7 Hz),3.57 (2H, dd, J=6, 12 Hz), 3.71 (2H, br.s, OH×2), 3.80 (2H, dd, J=6, 12Hz), 5.88 (1H, s), 6.54 (1H, d, J=3.4 Hz), 6.58 (1H, d, J=3.4 Hz)

IR(KBr): 3277, 2924, 2852, 1626, 1560, 1236, 1064, 1036 cm⁻¹

elemental analysis : calculated C 64.19, H 9.36, N 3.94 C₁₉ H₃₃ NO₃ Sfound C 63.75, H 9.17, N 3.68

MS: 355 (M⁺)

(8) 2-Amino-2- 2-(5-octyl-2-thienyl)ethyl!-1,3-propanediol hydrochloride

A aqueous solution (5 ml) of lithium hydroxide (380 mg) was added to asolution (5 ml) of the above-mentioned compound (500 mg) in methanol andthe mixture was refluxed under heating for 5 hours. The reaction mixturewas concentrated and extracted with ethyl acetate. The extract waswashed with saturated brine and dried over anhydrous sodium sulfate. Thesolvent was distilled away, whereby a powder was obtained. The powderwas dissolved in ethanol (3 ml) and a 26% solution (2 ml) ofhydrochloric acid in ethanol was added thereto. The solvent wasdistilled away and the precipitated crystals were recrystallized fromhexane-ethyl acetate to give 150 mg of the subject compound.

melting point: 63°-65° C.

¹ H-NMR (CD₃ OD) δ: 0.79 (3H, t, J=7 Hz), 1.18 (10H, m), 1.53 (2H, m),1.96 (2H, m), 2.63 (2H, t, J=7.8 Hz), 2.74 (2H, m), 3.61 (2H, d, J=12.2Hz), 3.67 (2H, d, J=12.2 Hz), 6.47 (1H, d, J=3.4 Hz), 6.54 (1H, d, J=3.4Hz)

IR(KBr): 3482, 3265, 1631, 1530, 1468, 1059, 811 cm⁻¹

elemental analysis : calculated C 58.35, H 9.22, N 4.00 C₁₇ H₃₁ NO₂ SHCl found C 58.12, H 9.25, N 4.03

MS: 313 (M⁺)

EXAMPLE 294 2-Amino-2-(4-octylsulfinylbenzyl)-1,3-propanediol

(1) 2-Acetamido-1,3-diacetoxy-2-(4-octylthiobenzyl)propane

Acetic anhydride (0.67 ml) was added to a solution (30 ml) of2-acetamido-2-(4-octylthiobenzyl)-1,3-propanediol (1.04 g) in pyridineand the mixture was stirred at room temperature for 4 hours. Thereaction mixture was concentrated and a 5% aqueous ammonium chloridesolution was added thereto. The mixture was extracted with ethylacetate. The ethyl acetate layer was washed with water and dried overanhydrous magnesium sulfate. The solvent was distilled away and theresidue was purified by silica gel column chromatography (eluent; ethylacetate:hexane=4:1) to give 0.73 g of the subject compound.

melting point=71°-74° C.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=6.9 Hz), 1.10-1.85 (12H, m), 1.94 (3H,s), 2.06 (6H, s), 2.28 (2H, t, J=7.8 Hz), 3.19 (2H, s), 4.26 (4H, dd,J=11.2, 17.6 Hz), 5.48 (1H, br.s), 7.03 (2H, d, J=8.3 Hz), 7.20 (2H, d,J=8.3 Hz)

IR(KBr): 3295, 2924, 1739 cm⁻¹

MS: 451 (M⁺)

elemental analysis: calculated C 63.83, H 8.26, N 3.10 found C 64.00, H8.32, N 3.12

(2) 2-Acetamido-1,3-diacetoxy-2-(4-octylsulfinylbenzyl)propane

To a solution (15 ml) of the above-mentioned compound (0.73 g) inchloroform was added m-chloroperbenzoic acid (0.56 g) and the mixturewas stirred for 40 minutes. Calcium hydroxide (0.23 g) was added to thereaction mixture and the mixture was stirred at room temperature for 1hour. The insoluble matters were filtered off and the solvent wasdistilled away. The residue was purified by silica gel columnchromatography (eluent; dichloromethane:methanol=30:1) to give 0.66 g ofthe subject compound.

melting point=70°-72° C.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=7.3 Hz), 1.10-1.80 (12H, m), 1.95 (3H,s), 2.07 (6H, s), 2.76 (2H, m), 3.33 (2H, s), 4.09-4.16 (4H, m), 5.54(1H, s), 7.29 (2H, d, J=8.3 Hz), 7.54 (2H, d, J=8.3 Hz)

IR(KBr): 3278, 3081, 2928, 1746, 1672, 1218 cm⁻¹

MS: 467 (M⁺)

elemental analysis: calculated C 61.65, H 7.97, N 3.00 found C 61.36, H7.90, N 2.93

(3) 2-Amino-2-(4-octylsulfinylbenzyl)-1,3-propanediol

An aqueous solution (3 ml) of lithium hydroxide (242 mg) was added to asolution (3 ml) of the above-mentioned compound (300 mg) in methanol andthe mixture was stirred at 50° C. for 5 hours. After concentration, thereaction mixture was extracted with ethyl acetate and washed with water.The mixture was dried over anhydrous magnesium sulfate and the solventwas distilled away. The residue was recrystallized from ethylacetate-hexane to give 81.5 mg of the subject compound.

melting point: 80°-82° C.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=6.8 Hz), 1.20-1.80 (16H, m), 2.70-2.90(4H, m), 3.44 (4H, dd, J=10.3, 17.1 Hz), 7.38 (2H, d, J=7.8 Hz), 7.55(2H, d, J=7.8 Hz)

IR(KBr): 3339, 2915, 2758, 1033 cm⁻¹

MS: 242 (M⁺)

elemental analysis: calculated C 63.31, H 9.15, N 4.10 found C 62.62, H9.04, N 3.91

EXAMPLE 295 2-Amino-2-(4-octylsulfonylbenzyl)-1,3-propanediol

(1) 2-Acetamido-1,3-diacetoxy-2-(4-octylsulfonylbenzyl)propane

To a solution (10 ml) of2-acetamido-1,3-diacetoxy-2-(4-octylsulfinylbenzyl)propane (330 mg) inchloroform was added m-chloroperbenzoic acid (244 mg) under ice-cooling.The mixture was stirred for 2.5 hours and then at room temperature for1.5 hours. Calcium hydroxide (0.1 g) was added to the reaction mixtureand the mixture was stirred at room temperature for 45 minutes. Theinsoluble matters were filtered off and the filtrate was concentratedunder reduced pressure. The residue was recrystallized from hexane-ethylacetate to give 162 mg of the subject compound.

melting point=98°-100° C.

¹ H-NMR (CDCl₃) δ: 0.84 (3H, t, J=7.3 Hz), 1.10-1.80 (12H, m), 1.96 (3H,s), 2.07 (6H, s), 3.06 (2H, m), 3.38 (2H, s), 4.25 (4H, dd, J=11.7, 25.8Hz), 5.54 (1H, s), 7.34 (2H, d, J=8.2 Hz), 7.81 (2H, d, J=8.2 Hz)

IR(KBr): 3317, 2921, 2853, 1749, 1654, 1313, 1141 cm⁻¹

MS: 483 (M⁺)

elemental analysis: calculated C 59.61, H 7.71, N 2.90 found C 59.50, H7.60, N 2.85

(2) 2-Amino-2-(4-octylsulfonylbenzyl)-1,3-propanediol

An aqueous solution (2.5 ml) of lithium hydroxide (109 mg) was added toa solution (2.5 ml) of the above-mentioned compound (140 mg) in methanoland the mixture was stirred at 50° C. for 4 hours. The reaction mixturewas extracted with ethyl acetate and the extract was washed with water.The mixture was dried over anhydrous magnesium sulfate and the solventwas distilled away. The residue was recrystallized from hexane-ethylacetate to give 45 mg of the subject compound.

melting point=108°-109° C.

¹ H-NMR (CDCl₃) δ: 0.84 (3H, t, J=7.3 Hz), 1.10-1.86 (16H, m), 2.83 (2H,s), 3.06 (2H, m), 3.43 (2H, s), 3.44 (2H, s), 7.43 (2H, d, J=7.8 Hz),7.82 (2H, d, J=7.8 Hz)

IR(KBr): 3343, 2915, 1299, 1147 cm⁻¹

MS: 357 (M⁺)

elemental analysis: calculated (0.1H₂ O) C 60.17, H 8.75, N 3.90 found C59.89, H 8.79, N 3.91

EXAMPLE 296 2-Amino-2- 2-(3-octylphenyl)ethyl!-1,3-propanediol andhydrochloride thereof

(1) 1-(3-Bromophenyl)octanol

A small amount of iodine was added to a solution (100 ml) of magnesium(9.8 g) in anhydrous tetrahydrofuran and the mixture was stirred at 50°C. until the color of the iodine disappeared. A solution of heptylbromide in anhydrous tetrahydrofuran (200 ml) was dropwise added theretoover 1 hour. The mixture was stirred at 65° C. for 1 hour and a solutionof m-bromobenzaldehyde in anhydrous tetrahydrofuran (200 ml) wasdropwise added thereto under ice-cooling. The mixture was stirred atroom temperature for 30 minutes. Under ice-cooling, a saturated aqueousammonium chloride solution (7.3 ml) was added thereto and the mixturewas stirred for 1 hour. The insoluble matters were filtered off and thefiltrate was concentrated. The concentrate was dissolved in ethylacetate and the mixture was washed with water. The mixture was driedover magnesium sulfate and the solvent was distilled away. The residueobtained was purified by silica gel column chromatography (eluent;hexane:ethyl acetate=10:1) to give 50.9 g of the subject compound as anoily substance.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=6.8 Hz), 1.20-1.90 (13H, m), 4.61 (1H,m), 7.1-7.3 (2H, m), 7.36 (1H, dr, J=1.5, 7.8 Hz), 7.49 (1H, m)

IR(neat): 3346, 2922, 2853cm⁻¹

MS: 285 (M⁺)

elemental analysis: calculated C 58.96, H 7.42, N 0.00 found C 58.92, H7.36, N 0.00

(2) trans-1-(3-Bromophenyl)-1-octene

Phosphorus pentaoxide (24.9 g) was added to a solution of theabove-mentioned compound (10 g) in benzene (500 ml) and the mixture wasrefluxed under heating for 1.5 hours. The insoluble matters werefiltered off, and the filtrate was washed with water and dried overanhydrous magnesium sulfate. The solvent was distilled away and theresidue was purified by silica gel column chromatography (eluent;hexane:ethyl acetate=20:1) to give 9 g of the subject compound as anoily substance.

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6.9 Hz), 1.20-1.50 (8H, m), 2.19 (2H,dt, J=6.3, 6.5 Hz), 6.21 (1H, td, J=6.3, 16.1 Hz), 6.28 (1H, d, J=16.1Hz), 7.13 (1H, t, J=7.9 Hz), 7.21 (1H, m), 7.28 (1H, m), 7.47 (1H, m)

IR(neat): 3439, 3063 cm⁻¹

MS: 267 (M⁺)

(3) trans-1-(3-Formylphenyl)-1-octene

A small amount of iodine was added to a solution of magnesium (1.38 g)in anhydrous tetrahydrofuran (30 ml) and the mixture was stirred at 50°C. until the color of the iodine disappeared. A solution of theabove-mentioned compound (13.8 g) in anhydrous tetrahydrofuran (40 ml)was dropwise added thereto over 30 minutes. The mixture was stirred at55° C. for 1 hour and a solution of dimethylformamide (4 ml) inanhydrous tetrahydrofuran (30 ml) was dropwise added thereto over 1hour. The mixture was stirred at room temperature for 2 hours. Underice-cooling, a saturated aqueous ammonium chloride solution was addedthereto and the mixture was extracted with ethyl acetate. The ethylacetate layer was washed with water and dried over magnesium sulfate.The solvent was distilled away and the residue obtained was purified bysilica gel column chromatography (eluent; hexane:ethyl acetate=30:1) togive 7.12 g of the subject compound as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6.8 Hz), 1.20-1.60 (8H, m), 2.22 (2}{,dt, J=6.8, 6.9 Hz), 6.32 (1H, td, J=6.8, 15.7 Hz), 6.41 (1H, d, J=15.7Hz), 7.43 (1H, t, J=7.8 Hz), 7.57 (1H, m), 7.68 (1H, m), 7.83 (1H, s),9.99 (1H, s)

IR(neat): 2956, 2927, 2855, 1699 cm⁻¹

MS: 216 (M⁺)

elemental analysis: calculated C 83.29, H 9.32 found C 83.50, H 9.29

(4) 3-(trans-1-Octenyl)-β-methylsulfinyl-β-methylthiostyrene

Methyl methyl sulfinyl methyl sulfide (3 ml) and a solution (2.6 ml) oftrimethylbenzyl ammonium hydroxide in methanol were added to a solutionof the above-mentioned compound (6.17 g) in dioxane (30 ml) and themixture was stirred at 80° C. for 2 hours. The reaction mixture wasconcentrated, dissolved in ethyl acetate and washed with water. Themixture was dried over anhydrous magnesium sulfate. The solvent wasdistilled away and the residue obtained was purified by silica gelcolumn chromatography (eluent; hexane:ethyl acetate=4:1) to give 6.48 gof the subject compound as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6.8 Hz), 1.20-1.55 (8H, m), 2.12 (2H,dr, J=6.8, 6.9 Hz), 2.30 (3H, s), 2.75 (3H, s), 6.25 (1H, td, J=6.8,16.1 Hz), 6.37 (3H, t, J=16.1 Hz), 7.30-7.40 (2H, m), 7.60 (1H, s), 7.72(1H, m), 7.81 (1, s)

IR(neat): 2955, 2925, 1068 cm⁻¹

MS: 322 (M⁺)

(5) Ethyl 3-(trans-1-octenyl)phenylacetate

A solution of 26% hydrogen chloride in ethanol (48 ml) was added to asolution of the above-mentioned compound (6.48 g) in ethanol (40 ml) andthe mixture was stirred at room temperature for 1 hour. The reactionmixture was concentrated and the residue was purified by silica gelcolumn chromatography (eluent; hexane:ethyl acetate=20:1) to give 5.11 gof the subject compound as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6.8 Hz), 1.18-1.50 (11H, m) 2.19 (2H,dr, J=6.8, 6.9 Hz), 3.57 (2H, s), 4.13 (2H, q, J=7.3 Hz), 6.22 (1H, td,J=6.8, 16.1 Hz), 6.33 (1H, d, J=16.1Hz), 7.10-7.25

IR(neat): 2957, 2927, 2855, 1737 cm⁻¹

MS: 274 (M⁺)

(6) 2- 3-(trans-1-Octenyl)phenyl!ethanol

Lithium aluminum hydride (1.22 g) was suspended in anhydroustetrahydrofuran (150 ml) and thereto was added the above-mentionedcompound (5.89 g) under ice-cooling. The mixture was stirred for 1 hour.Under ice-cooling, ethanol and water were added thereto and theinsoluble matters were filtered off. The filtrate was dried overanhydrous sodium sulfate and the solvent was distilled away. The residuewas purified by silica gel column chromatography (eluent; hexane: ethylacetate=5:1) to give 4.22 g of the subject compound as an oilysubstance.

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6.8 Hz), 1.10-1.50 (8H, m), 2.19 (2H,dt, J=6.8, 6.9 Hz), 2.83 (2H, t, J=6.3 Hz), 3.85 (2H, dr, J=6.2, 6.3Hz), 6.20 (1H, td, J=6.8, 16.1 Hz), 6.34 (1H, d, J=16.1 Hz), 7.03 (1H,m), 7.18-7.27(3H, m)

IR(neat): 3348, 2956, 2926, 2854 cm⁻¹

MS: 232 (M⁺)

(7) 2- 3-(trans-1-Octenyl)phenyl!ethylmethanesulfonate

Triethylamine (2.8 ml) was added to a solution (60 ml) of theabove-mentioned compound (4.19 g) in dichloromethane and the mixture wasice-cooled. Thereto was dropwise added methanesulfonyl chloride (14 ml)and the mixture was stirred at room temperature for 1.5 hours. Thereaction mixture was poured into ice water and extracted withdichloromethane. The dichloromethane layer was washed with a saturatedpotassium hydrogencarbonate solution, a 1% aqueous hydrochloric acidsolution and saturated brine and dried over anhydrous magnesium sulfate.The solvent was distilled away and the residue was purified by silicagel column chromatography (eluent; hexane:ethyl acetate=5:1) to give5.55 g of the subject compound as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6.8 Hz), 1.20-1.50 (8H, m), 2.19 (2H,dt, J=6.8, 6.9 Hz), 2.83 (3H, s), 3.02 (2H, t, J=6.8 Hz), 4.40 (2H, t,J=6.8 Hz), 6.22 (1H, td, J=6.8, 15.6 Hz), 6.33 (1H, d, J=15.6 Hz), 7.03(1H, m), 7.18-7.24 (3H, m)

IR(neat): 2956, 2927, 2855 cm⁻¹

MS: 310 (M⁺)

(8) 2- 3-(trans-1-Octenyl)phenyl!ethyl iodide

Sodium iodide (3.99 g) was added to a solution of the above-mentionedcompound (5.51 g) in 2-butanone (60 ml) and the mixture was stirred at45° C. for 3 hours. The reaction mixture was concentrated, poured intoice water and extracted with ethyl acetate. The extract was washed withsaturated brine and dried over anhydrous magnesium sulfate. The solventwas distilled away and the residue was purified by silica gel columnchromatography (eluent; hexane:ethyl acetate=100:1) to give 4.75 g ofthe subject compound as an oily substance.

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6.8 Hz), 1.20-1.50 (8H, m), 2.19 (2H,dr, J=6.8, 6.9 Hz), 3.14 (2H, t, J=7.4 Hz), 3.34 (2H, t, J=7.4 Hz), 6.21(1H, td, J=6.8, 18.1 Hz), 6.34 (1H, d, J=18.1 Hz), 7.00 (1H, m),7.14-7.24 (3H, m)

IR(neat): 2956, 2925, 2853 cm⁻¹

MS: 342 (M⁺)

(9) Diethyl 2-acetamido-2- 2- 3-(trans-1-octenyl)phenyl)ethyl!malonate

Sodium ethoxide (1.62 g) was added to a solution of diethylacetamidomalonate (7.62 g) in ethanol (30 ml) and the mixture wasstirred at 60° C. for 45 minutes. Thereto was dropwise added a solutionof the above-mentioned compound (4 g) in ethanol (20 ml) and the mixturewas refluxed under heating for 5 hours. The reaction mixture wasconcentrated, poured into ice water and extracted with ethyl acetate.The extract was washed with saturated brine and dried over anhydrousmagnesium sulfate. The solvent was distilled away and the residue waspurified by silica gel column chromatography (eluent; hexane:ethylacetate=3:1) to give 2.46 g of the subject compound as an oilysubstance.

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6.9 Hz), 1.22 (6H, t, J=6.8 Hz),1.22-1.50 (8H, m), 1.97 (3H, s), 2.17 (2H, dr, J=6.8, 6.9 Hz), 2.43 (2H,m), 2.67 (2H, m), 4.11-4.23 (4H, m), 6.18 (1H, td, J=6.8, 16.1 Hz), 6.31(1H, d, J=16.1 Hz), 6.74 (1H, s), 6.94 (1H, d, J=6.8 Hz), 7.09-7.18 (3H,m)

IR(neat): 3413, 2957, 2927, 1741, 1683 m⁻¹

MS: 431 (M⁺)

elemental analysis: calculated (1/10 H₂ O) C 69.29, H 8.65, N 3.23 foundC 69.04, H 8.75, N 3.26

(10) 2-Acetamido-1,3-diacetoxy-2-2-(3-(trans-1-octenyl)phenyl)ethyl!propane

The above-mentioned compound (2.8 g) in anhydrous tetrahydrofuran (20ml) was dropwise added to a solution of lithium aluminum hydride (0.74g) in anhydrous tetrahydrofuran (40 ml) in a stream of nitrogen underice-cooling and the mixture was stirred at room temperature for 2 hours.Under ice-cooling, ethanol and water were added to the reaction mixtureand the insoluble matters were filtered off. The filtrate was dried overanhydrous magnesium sulfate and the solvent was distilled away to give ayellow, oily substance (2.34 g). This substance was dissolved inpyridine (60 ml) and thereto was added acetic anhydride (1.6 ml) underice-cooling. The mixture was stirred at room temperature for 2.5 hours.The reaction mixture was concentrated and the residue was dissolved inethyl acetate. The mixture was washed with a saturated aqueous ammoniumchloride and saturated brine and dried over anhydrous magnesium sulfate.The solvent was distilled away and the residue was purified by silicagel column chromatography (eluent; hexane:ethyl acetate=4:1) to give 1.8g of the subject compound as white crystals.

melting point=84°-86° C.

¹ H-NMR (CDCl₃) δ: 0.87 (3H, t, J=6.8 Hz), 1.10-1.50 (8H, m), 1.94 (3H,s), 2.07 (6H, s), 2.15-2.21 (4H, m), 2.57 (2H, m), 4.33 (4H, s), 5.62(1H, s), 6.19 (1H, dt, J=6.8, 16.1 Hz), 6.33 (1H, d, J=16.1 Hz), 6.99(1H, d, J=6.8 Hz), 7.13-7.21 (3H, m)

IR(KBr): 3311, 2961, 2926, 1738, 1652 cm⁻¹

MS: 431 (M⁺)

elemental analysis : calculated C 69.58, H 8.64, N 3.25 found C 69.85, H8.74, N 3.35

(11) 2-Acetamido-1,3-diacetoxy-2- 2-(3-(octylphenyl)ethyl!propane

A suspension of 10% palladium carbon (150 mg) in methanol (10 ml) wasadded to a solution of the above-mentioned compound (1.41 g) in methanol(10 ml) and the mixture was stirred under hydrogen pressurization (10atm) for 2 hours. The inside of the reaction vessel was displaced withnitrogen and the insoluble matters were filtered off. The solvent wasdistilled away and the residue was purified by silica gel columnchromatography (eluent; hexane:ethyl acetate=2:1) to give 1.05 g of thesubject compound as white crystals.

melting point=86°-87° C.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6.9 Hz), 1.10-1.60 (12H, m), 1.93 (3H,s), 2.07 (6H, s), 2.18 (2H, m), 2.52 (2H, t, J=6.8 Hz), 2.56 (2H, t,J=6.8 Hz), 4.33 (4H, s), 5.61 (1H, s), 6.95-7.05 (3H, m), 7.17 (1H, t,J=7.8 Hz)

IR(KBr): 3313, 2960, 2925, 2854, 1738, 1651 cm⁻¹

(12) 2-Amino-2- 2-(3-octylphenyl)ethyl!-1,3-propanediol

An aqueous solution (10 ml) of lithium hydroxide (1 g) was added to asolution of the above-mentioned compound (1.04 g) in methanol (10 ml)and the mixture was refluxed under heating for 5 hours. The reactionmixture was concentrated, extracted with ethyl acetate and washed withsaturated brine. The mixture was dried over anhydrous magnesium sulfateand the solvent was distilled away. The residue was purified by silicagel column chromatography (eluent; chloroform:methanol=5:1) to give 0.46g of the subject compound as white crystals.

melting point=89°-92° C.

¹ H-NMR (CDCl₃) δ: 0.85 (3H, t, J=6.4 Hz), 1.20-1.35 (12H, m), 1.55 (2H,m), 1.83 (2H, m), 2.51 (2H, t, J=7.2 Hz), 2.60 (2H, m), 2.98 (2H, br.s),3.68 (2H, t, J=11.2 Hz), 3.71 (2H, t, J=11.2 Hz), 6.97 (3H, m), 7.12(1H, t, J=7.3 Hz)

IR(KBr): 3396, 3257, 2925, 2854 cm⁻¹

(13) 2-Amino-2- 3-(3-octylphenyl)ethyl!-1,3-propanediol hydrochloride

The above-mentioned compound (0.45 g) was dissolved in ethanol (20 ml)and thereto was added a 26% solution (1 ml) of hydrochloric acid inethanol. The solvent was distilled away and the precipitated crystalswere recrystallized from ethyl acetate:methanol=30:1 to give 0.33 g ofthe subject compound.

melting point=99°-101° C.

¹ H-NMR (DMSO) δ: 0.84 (3H, t, J=6.8 Hz), 1.20-1.35 (12H, m), 1.53 (2H,m), 1.74 (2H, m), 2.40-2.60 (2H, m), 3.45 (4H, s), 5.33 (2H, br.s),6.98-7.00 (3H, m), 7.18 (1H, t, J=7.3 Hz), 7.70 (3H, br.s)

IR(KBr): 3178, 2924, 2853 cm⁻¹

EXAMPLE 297 2-Amino-2-(4-decylphenyl)-1,3-propanediol

(1) 4-Bromomethyldecylbenzene

4-Decylphenylmethanol (3.91 g) was dissolved in toluene (40 ml) andthereto was added 48% hydrobromic acid (40 ml). The mixture was refluxedunder heating at 90° C. for 6 hours. After cooling, the organic layerwas separated and washed with saturated brine and a sodiumhydrogencarbonate solution. The mixture was dried over anhydrous sodiumsulfate and the solvent was distilled away to give 4.9 g of the oilysubject compound.

¹ H-NMR (CDCl₃) δ: 0.86 (3H, t, J=6.6 Hz), 1.2-1.3 (14H, m), 1.5-1.6(2H, m), 2.57 (2H, t, J=7.6 Hz), 4.47 (2H, s), 7.13 (2H, d, J=8.1 Hz),7.28 (2H, d, J=8.0 Hz)

(2) 4-Decylphenylnitromethane

Silver nitrite (4.15 g) and dry ether (20 ml) were placed in a flask andcooled with ice. Thereto was dropwise added a solution of4-bromomethyldecylbenzene (5.5 g) in ether (10 ml) with stirring. Afterthe dropwise addition, the mixture was stirred under ice-cooling for 4hours and the insoluble matters were filtered off. The solvent in thefiltrate was distilled away and the residue was crystallized frompentane to give 1.44 g of the subject compound as pale yellow crystals.

melting point=50° C.

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6 Hz), 1.2-1.3 (14H, m), 1.5-1.6 (2H,m), 2.62 (2H, t, J=8 Hz), 5.41 (2H, s), 7.24 (2H, d, J=8 Hz), 7.28 (2H,d, J=8 Hz)

(3) 2-(4-Decylphenyl)-2-nitro-1,3-propanediol

4-Decylphenylnitromethane (555 mg) was dissolved in ethanol (5 ml) andthereto were added a 1N aqueous sodium hydroxide solution (0.02 ml) and37% formalin (0.45 ml). The mixture was heated at 50° C. for 6 hours.The solvent was distilled away and the residue was extracted with ethylacetate. The extract was washed with saturated brine and dried overanhydrous sodium sulfate. The solvent was distilled away and the residuewas crystallized from hexane to give 1.75 g of the colorless, scale-likesubject compound.

melting point=80°-81° C.

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6 Hz), 1.2-1.3 (14H, m), 1.5-1.6 (2H,m), 2.59 (2H, t, J=8 Hz), 2.77 (2H, m), 4.35 (2H, m), 4.60 (2H, m), 7.17(2H, d, J=10 Hz), 7.21 (2H, d, J=10 Hz)

(4) 2-Amino-2-(4-decylphenyl)-1,3-propanediol

2-(4-Decylphenyl)-2-nitro-1,3-propanediol (170 mg) was dissolved inethanol (30 ml) and the mixture was subjected to catalytic reduction inthe presence of 5% palladium carbon (40 mg) under hydrogen pressure of20 atm. After stirring the mixture for 8 hours, the insoluble matterswere filtered off and the filtrate was concentrated. The residue waspurified by preparative thin layer chromatography (silica gel) to give8.9 mg of the subject compound.

melting point=136°-137° C.

¹ H-NMR (CDCl₃ --CD₃ OD) δ: 0.88 (3H, t, J=8 Hz), 1.1-1.4 (14H, m),1.4-1.8 (2H, m), 2.3-2.7 (GH, m), 3.5-4.2 (4H, m), 7.2 (2H, d, J=10 Hz),7.33 (2H, d, J=10 Hz)

melting point of hydrochloride=113°-114° C. (recrystallized fromisopropyl alcohol)

EXAMPLE 298 2-Acetylamino-2-(4-decylphenyl)-1,3-propanediol

2-Amino-2-(4-decylphenyl)-1,3-propanediol (313 mg) was dissolved in amixed solvent of ethanol (20 ml) and chloroform (5 ml). Thereto wasadded triethylamine (0.4 ml) and the mixture was cooled to -60° C. withdry ice-methanol. Thereto was dropwise added a solution of acetylchloride (0.12 ml) in dichloromethane (5 ml) under ice-cooling and themixture was heated to room temperature. The solvent was distilled awayand the residue was dissolved in ethyl acetate. The mixture was washedwith brine, an aqueous dilute hydrochloric acid solution and an aqueoussodium hydrogencarbonate solution. The resultant mixture was dried overanhydrous sodium sulfate and the solvent was distilled away. The residuewas purified by preparative thin layer chromatography (silica gel) andrecrystallized from hexane to give 130 mg of the colorless, crystallinesubject compound.

melting point=112-113° C.

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6.9 Hz), 1.2-1.4 (14H, m), 1.5-1.7(2H, m), 2.17 (3H, s), 2.58 (2H, t, J=7.9 Hz), 3.66 (2H, dd, J=7.7 Hz, 6Hz), 3.88 (2H, dd, J=12 Hz, 7.6 Hz), 4.05 (2H, dd, J=11.9 Hz, 6 Hz),6.37 (1H, bs), 7.20 (2H, d, J=8.6 Hz), 7.25 (2H, d, J=8.6 Hz)

EXAMPLE 299 5-Acetamido-5-(4-decylphenyl)-2,2-dimethyl-1,3-dioxane

2-Acetylamino-2-(4-decylphenyl)-1,3-propanediol (224 mg) and2,2-dimethoxypropane (0.3 ml) were dissolved in benzene (5 ml) and themixture was refluxed under heating in the presence of a catalytic amountof toluenesulfonic acid. After cooling, the reaction mixture was washedwith an aqueous sodium hydrogencarbonate solution and dried over sodiumsulfate. The solvent was distilled away and the residue was purified bypreparative thin layer chromatography (silica gel) to give 99 mg of theamorphous subject compound.

¹ H-NMR (CDCl₃) δ: 0.88 (3H, t, J=6.6 Hz), 1.2-1.4 (14H, m), 1.48 (3H,s), 1.51 (3H, s), 1.5-1.7 (2H, m), 2.06 (3H, s), 2.56 (2H, t, J=7.8 Hz),4.14 (4H, s), 6.23 (1H, bs), 7.15 (2H, d, J=8.3 Hz), 7.22 (2H, d, J=8.3Hz)

EXAMPLE 300 2-Amino-2-(8-phenyloctyl)-1,3-propanediol EXAMPLE 3012-Amino-2-(9-phenylnonyl)-1,3-propanediol EXAMPLE 3022-Amino-2-(11-phenylundecyl)-1,3-propanediol EXAMPLE 3032-Amino-2-(12-phenyldodecyl)-1,3-propanediol EXAMPLE 3042-Amino-2-(14-phenyltetradecyl)-1,3-propanediol EXAMPLE 3052-Amino-2-(15-phenylpentadecyl)-1,3-propanediol EXAMPLE 3062-Amino-2-(16-phenylhexadecyl)-1,3-propanediol EXAMPLE 307 2-Amino-2-2-(4-tridecylphenyl)ethyl!-1,3-propanediol EXAMPLE 308 2-Amino-2-2-(4-tetradecylphenyl)ethyl!-1,3-propanediol EXAMPLE 309 2-Amino-2-2-(4-hexyloxyphenyl)ethyl!-1,3-propanediol EXAMPLE 310 2-Amino-2-2-(4-decyloxyphenyl)ethyl!-1,3-propanediol EXAMPLE 311 2-Amino-2-2-(4-dodecyloxyphenyl)ethyl!-1,3-propanediol EXAMPLE 312 2-Amino-2-2-(4-tridecyloxyphenyl)ethyl!-1,3-propanediol EXAMPLE 313 2-Amino-2-2-(4-(8-fluorooctyl)phenyl)ethyl!-1,3-propanediol EXAMPLE 314 2-Amino-2-2-(4-(12-fluorododecyl)phenyl)ethyl!-1,3-propanediol EXAMPLE 3152-Amino-2- 2-(4-(7-fluoroheptyloxy)phenyl)ethyl!-1,3-propanediol EXAMPLE316 2-Amino-2- 2-(4-(11-fluoroundecyloxy)phenyl)ethyl!-1,3-propanediolEXAMPLE 317 2-Amino-2- 2-(4-phenylmethyloxyphenyl)ethyl!-1,3-propanediolEXAMPLE 318 2-Amino-2-2-(4-(2-phenylethyloxy)phenyl)ethyl!-1,3-propanediol EXAMPLE 3192-Amino-2- 2-(4-(3-phenylpropyloxy)phenyl)ethyl!-1,3-propanediol EXAMPLE320 2-Amino-2- 2-(4-(4-phenylbutyloxy)phenyl)ethyl!-1,3-propanediolEXAMPLE 321 2-Amino-2-2-(4-(5-phenylpentyloxy)phenyl)ethyl!-1,3-propanediol EXAMPLE 3222-Amino-2- 2-(4-(7-phenylheptyloxy)phenyl)ethyl!-1,3-propanediol EXAMPLE323 2-Amino-2- 2-(4-(8-phenyloctyloxy)phenyl)ethyl!-1,3-propanediolEXAMPLE 324 2-Amino-2-4-(6-(4-fluorophenyl)hexyloxy)phenyl)ethyl!-1,3-propanediol EXAMPLE 3252-Amino-2- 2-(4-(4-phenoxybutyloxy)phenyl)ethyl!-1,3-propanediol EXAMPLE326 2-Amino-2- 2-(4-(5-phenoxypentyloxy)phenyl)ethyl!-1,3-propanediolEXAMPLE 327 2-Amino-2-2-(4-(6-phenoxyhexyloxy)phenyl)ethyl!-1,3-propanediol EXAMPLE 3282-Amino-2- 2-(4-(7-phenoxyheptyloxy)phenyl)ethyl!-1,3-propanediolEXAMPLE 329 2-Amino-2-2-(4-(4-phenoxybutyl)phenyl)ethyl!-1,3-propanediol EXAMPLE 3302-Amino-2- 2-(4-(5-phenoxypentyl)phenyl)ethyl!-1,3-propanediol EXAMPLE331 2-Amino-2- 2-(4-(6-phenoxyhexyl)phenyl)ethyl!-1,3-propanediolEXAMPLE 332 2-Amino-2-2-(4-(7-phenoxyheptyl)phenyl)ethyl!-1,3-propanediol EXAMPLE 3332-Amino-2- 2-(4-octylcyclohexyl)ethyl!-1,3-propanediol EXAMPLE 3342-Amino-2- 2-(4-nonylcyclohexyl)ethyl!-1,3-propanediol EXAMPLE 3352-Amino-2- 2-(4-dodecylcyclohexyl)ethyl!-1,3-propanediol EXAMPLE 3362-Amino-2- 2-(1-octylpiperidin-4-yl)ethyl!-1,3-propanediol EXAMPLE 3372-Amino-2- 2-(1-dodecylpiperidin-4-yl)ethyl!-1,3-propanediol EXAMPLE 3382-Amino-2- 2-(5-nonyl-2-thienyl)ethyl!-1,3-propanediol EXAMPLE 3392-Amino-2- 2-(5-decyl-2-thienyl)ethyl!-1,3-propanediol EXAMPLE 3402-Amino-2- 2-(5-dodecyl-2-thienyl)ethyl!-1,3-propanediol EXAMPLE 3412-Amino-2- 13-(2-thienyl)tridecyl!-1,3-propanediol EXAMPLE 3422-Amino-2- 2-(5-octyl-2-pyridyl)ethyl!-1,3-propanediol EXAMPLE 3432-Amino-2- 2-(5-decyl-2-pyridyl)ethyl!-1,3-propanediol EXAMPLE 3442-Amino-2- 13-(2-pyridyl)tridecyl!-1,3-propanediol EXAMPLE 3452-Amino-2- 2-(2-octyl-5-pyridyl)ethyl!-1,3-propanediol EXAMPLE 3462-Amino-2- 2-(2-decyl-5-pyridyl)ethyl!-1,3-propanediol EXAMPLE 3472-Amino-2- 13-(3-pyridyl)tridecyl!-1,3-propanediol EXAMPLE 3482-Amino-2-(4-decylphenyl)-1,3-propanediol EXAMPLE 3492-Amino-2-(4-dodecylphenyl)-1,3-propanediol EXAMPLE 3502-Amino-2-(4-tetradecylphenyl)-1,3-propanediol EXAMPLE 3512-Amino-2-(4-hexadecylphenyl)-1,3-propanediol EXAMPLE 352 2-Amino-2-1-hydroxy-2-(4-octylphenyl)ethyl!-1,3-propanediol EXAMPLE 353 2-Amino-2-2-(4-dodecylphenyl)-1-hydroxyethyl!-1,3-propanediol EXAMPLE 3542-Amino-2- 2-(4-heptyloxyphenyl)-1-hydroxyethyl!-1,3-propanediol EXAMPLE355 2-Amino-2- 1-hydroxy-2-(4-undecyloxyphenyl)ethyl!-1,3-propanediolEXAMPLE 356 2-Amino-2-2-(4-(8-fluorooctyl)phenyl)-1-hydroxyethyl!-1,3-propanediol EXAMPLE 3572-Amino-2-2-(4-(12-fluorododecyl)phenyl)-1-hydroxyethyl!-1,3-propanediol EXAMPLE358 2-Amino-2-2-(4-(7-fluoroheptyloxy)phenyl)-1-hydroxyethyl!-1,3-propanediol EXAMPLE359 2-Amino-2-1-hydroxy-2-(4-(11-fluoroundecyloxy)phenyl)ethyl!-1,3-propanedio EXAMPLE360 2-Amino-2- 2-(4-octylphenyl)ethenyl!-1,3-propanediol EXAMPLE 3612-Amino-2- 2-(4-decylphenyl)ethenyl!-1,3-propanediol EXAMPLE 3622-Amino-2- 2-(4-dodecylphenyl)ethenyl!-1,3-propanediol EXAMPLE 3632-Amino-2- 2-(4-tetradecylphenyl)ethenyl!-1,3-propanediol EXAMPLE 3642-Amino-2-(4-octyl phenoxymethyl)-1,3-propanediol EXAMPLE 3652-Amino-2-(4-decylphenoxymethyl)-1,3-propanediol EXAMPLE 3662-Amino-2-(4-dodecylphenoxymethyl)-1,3-propanediol EXAMPLE 3672-Amino-2-(4-tetradecylphenoxymethyl)-1,3-propanediol EXAMPLE 3682-Amino-2-(1-hydroxy-2-phenylethyl)-1,3-propanediol hydrochloride

melting point=188°-190° C.

¹ H-NMR (DMSO-d₆) δ(ppm): 2.57 (1H, dd, J=10.7, 14.2 Hz), 2.88 (1H, d,J=14.2 Hz), 3.63 (4H, m),3.85 (1H, d, J=10.7 Hz), 5.16 (1H, br.s), 5.28(2H, br.s), 7.25 (5H, m), 7.77 (3H, br.s)

IR ν (KBr)_(max) : 3156, 2814, 1626, 1550, 1080, 1056, 743, 702 cm⁻¹

EXAMPLE 3692-Acetamido-1,3-diacetoxy-2-(1-acetoxy-2-phenylethyl)propane,transparent oil

¹ H-NMR (CDCl₃) δ(ppm): 1.89 (3H, s), 1.94 (3H, s), 2.08 (3H, s), 2.13(3H, s), 2.83 (1H, dd, J=10.3, 14.2 Hz), 3.05 (1H, dd, J=3.4, 14.2 Hz),4.46 (1H, d, J=11.7 Hz), 4.48 (1H, d, J=11.7 Hz), 4.55 (1H, d, J=11.7Hz), 4.71 (1H, d, J=11.7 Hz), 5.66 (1H, dd, J=3, 4, 10.3 Hz), 5.86 (1H,s, --NH), 7.22 (5H, m)

EXAMPLE 370 (Z)-2-Amino-2-styryl-1,3-propanediol

¹ H-NMR (CDCl₃) δ(ppm): 2,62 (4H, br.s), 3.47 (2H, d, J=11 Hz.), 3.55(2H, d, J=11 Hz), 5.55 (1H, d, J=12.7 Hz), 6.74 (1H, d, J=12.7 Hz), 7.27(5H, m)

EXAMPLE 371 (E)-2-Amino-2-styryl-1,3-propanediol

¹ H-NMR (CD₃ OD) δ(ppm): 3.51 (2H, d, J=11 Hz), 3.63 (2H, d, J=11 Hz),6.10 (1H, d, J=16.4 Hz), 6.55 (1H, d, J=16.4 Hz), 7.23 (5H, m)

EXAMPLE 372 2-Acetamido-2- 2-(4-decylphenyl)ethyl!-1,3-propanedioldiacetate

melting point=101°-104° C.

¹ H-NMR (CDCl₃) δ(ppm): 0.88 (3H, t, J=6 Hz), 1.26-1.29 (16H, m), 1.95(3H, s), 2.09 (6H, s), 2.17-2.21 (2H, m), 2.54-2.60 (4H, m), 4.35 (4H,s), 5.63 (1H, s), 7.09 (4H, s),

IR ν: 3310, 2919, 1735, 1654, 1231, 1058 cm⁻¹

EXAMPLE 373 2-Amino-2- 2-(4-decylphenyl)ethyl!-1,3-propanediolhydrochloride

melting point: 111°-115° C.

¹ H-NMR (CDCl₃) δ(ppm): 0.88 (3H, t, J=6 Hz), 1.26-1.29 (16H, s),1.92-1.96 (2H, m), 2.56 (2H, t, J=8 Hz), 2.61-2.65 (2H, m), 3.71 (4H, q,J=12 Hz), 7.11 (4H, s)

IR ν: 3373, 2923, 1603, 1518, 1070 cm⁻¹

EXAMPLE 374 2-Acetamido-2-2-(4-(4-methylpentyloxy)phenyl)ethyl!-1,3-propanediol diacetate

melting point: 83°-87° C.

¹ H-NMR (CDCl₃) δ(ppm): 0.91 (6H, d, J=6 Hz), 1.57 (4H, s), 1.96 (3H,s), 2.09 (6H, s), 2.15-2.19 (2H, m), 2.51-2.58 (2H, m), 3.91 (2H, t, J=6Hz), 4.34 (4H, s),6.81 (2H, d, J=4 Hz), 7.08 (2H, d, J=4 Hz)

IR ν: 3310, 2954, 1735, 1649 cm⁻¹

elemental analysis: calculated C 65.54, H 8.37, N 3.32 found C 65.60, H8.40, N 3.43

EXAMPLE 375 2-Amino-2-2-(4-(4-methylpentyloxy)phenyl)ethyl!-1,3-propanediol 1/10 hydrate

melting point=125°-128° C.

¹ H-NMR (CDCl₃) δ(ppm): 0.83 (6H, d, J=6 Hz), 1.25 (2H, t, J=6 Hz),1.54-1.58 (3H, m), 1.66-1.72 (2H, m), 2.47-2.51 (2H, m), 3.39-3.50 (4H,m), 3.81-3.85 (2H, m), 6.73 (2H, d, J=12 Hz), 7.02 (2H, d, J=12 Hz)

IR ν: 3324, 2951, 1513, 1247, 1026 cm⁻¹

EXAMPLE 376 2-Acetamido-2-(2-pyridylmethyl)-1,3-propanediol

¹ H-NMR (400 MHz, CDCl₃) δ(ppm): 1.66 (2H, br.s, OH), 1.94 (3H, s, CH₃),3.26 (2H, s, CH₂), 3.56 (4H,dd, J=72, 12 Hz, CH₂ ×2), 6.97 (1H, br.s,NH), 7.23 (1H, dd, J=8.0, 4.0 Hz, ArH), 7.33 (1H, d, J=8.0 Hz, ArH),7.69 (1H, dt, J=8.0, 4.0 Hz, ArH), 8.49 (1H, d, J=4.0 Hz, ArH)

EXAMPLE 377 2-Acetamido-2-(2-pyridylmethyl)-1,3-diacetoxypropane

¹ H-NMR (400 MHz, CDCl₃) δ(ppm): 1.96 (3H, s, CH₃), 2.05 (6H, s, CH₃×2), 3.13 (2H, s, CH₂), 4.47 (4H, dd, J=40, 12 Hz, CH₂ ×2), 7.15 (1H, d,J=8.0 Hz, ArH), 7.21 (1H, dd, J=8.0, 4.0 Hz, ArH), 7.48 (1H, s, NH),7.65 (1H, dt, J=8.0, 4.0 Hz, ArH), 8.55 (1H, d, J=4.0 Hz, ArH)

IR ν (KBr)_(max) : 3320(NH), 1748 (CO), 1654, 1533, 1248 cm⁻¹

MS: 308 (M⁺)

melting point=109°-110° C.

EXAMPLE 378 2-Amino-2-(2-pyridylmethyl)-1,3-propanediol 3/4 hydrate 2hydrochloride

¹ H-NMR (400 MHz, CD₃ OD) δ(ppm): 3.53 (2H, s, ArCH₂), 3.65 (4H, ddd,J=24, 12, 4.0 Hz, CH₂ ×2), 4.88 (6H, br.s, OH×2, N⁺ H₃, N⁺), 8.02 (1H,t, J=8.0 Hz, ArH), 8.09 (1H, d, J=8.0 Hz, ArH), 8.57-8.61 (1H, m, ArH),8.81 (1H, d, J=4.0 Hz, ArH)

IR ν (KBr)_(max) : 3385, 3070, 3059, 2945, 2897, 1621, 1066 cm⁻¹

MS: 183 (M⁺)

melting point=165-170° C.

EXAMPLE 379 2-Acetamido-2- 2-(5-butylpyridyl)methyl!-1,3-propanediol

¹ H-NMR (400 MHz, CDCl₃) δ(ppm): 0.94 (3H, t, d:8.0 Hz, CH₂), 1.26 (2H,t, J=8.0 Hz, CH₃), 1.36 (2H, m, CH₂), 1.59 (2H, br,s, OH×2), 1.93 (3H,s, CH₂), 2.58-2.62 (2H, m,CH₂), 3.21 (2H, s, CH₂), 3.55 (4H, dd, J=72,12 Hz, CH₂ ×2), 6.97 (1H, br.s, NH), 7.22 (1H, d, J=8.0 Hz, ArH),8.45-8.50 (1H, m, ArH), 8.31 (1H, br.s, ArH)

IR ν (neat)_(max) : 3378(OH), 2958, 2933, 2862, 1738(CO), 1658 cm⁻¹ oil

EXAMPLE 380 2-Acetamido-2-2-(5-butylpyridyl)methyl!-1,3-diacetoxypropane

¹ H-NMR (400 MHz, CDCl₃) δ(ppm): 0.94 (3H, t, J=8.0 Hz, CH₃), 1.33-1.42(2H, m, CH₂), 1.56-1.64 (2H, m, CH,), 1.96 (3H, s, CH₃), 2.05 (6H, s,CH₃ ×2), 2.60 (2H, t, J=8.0 Hz, CH₂), 3.08 (2H, s, CH₂), 4.46 (4H, dd,J=40, 12 Hz, CH₂ ×2), 7.05 (1H, d, J=8.0 Hz, ArH), 7.44-7.46 (1H, m,ArH), 7.56 (1H, s, NH), 8.35-8.37 (1H, m, ArH)

IR ν (KBr)_(max) : 3371, 3290, 2959, 2934, 1745(CO), 1681, 1240 cm⁻¹ oil

EXAMPLE 381 2-Amino-2- 2-(5-butylpyridyl)methyl!-1,3-propanediol

¹ H-NMR (400 MHz, CDCl₃) δ(ppm): 0.94 (3H, t, J=8.0 Hz, CH₂), 1.36 (2H,dt, J=16, 8.0 Hz, CH₂), 1.59 (2H, dt, J=16, 8.0 Hz, CH₂), 2.60 (2H, t,J=8.0 Hz, CH₂), 2.92 (2H, s, CH₂), 1.20-3.00 (4H, m, OH×2, NH₂), 3.39(4H, dd, J=36, 12 Hz, CH₂ ×2), 7.13 (1H, d, J=8.0 Hz, ArH), 7.48 (1H,dd, J=8.0, 2.0 Hz, ArH), 8.33 (1H, d, J=2.0 Hz, ArH)

IR ν (KBr)_(max) : 3339, 3269, 2923, 2857, 1595, 1033 cm⁻¹

melting point: 63°-65° C.

EXAMPLE 382 2-Acetamido-1,3-diacetoxy-2-2-(1-octylpiperidin-4-yl)ethyl!propane

melting point: 93°-95° C.

¹ H-NMR (CDCl₃) δ(ppm): 0.85 (3H, t, J=6.4 Hz), 1.19-1.36 (15H, m), 1.50(2H, br.s), 1.64 (2H, d, J=11.8 Hz), 1.85-1.97 (3H, m), 1.93 (3H, s),2.05 (6H, s), 2.33 (2H, br.s), 2.97 (2H, br.s), 4.25 (4H, s), 5.61 (1H,s)

IR ν (KBr)_(max) : 3302, 1739, 1654, 1560 cm⁻¹

EXAMPLE 383 2-Acetamido-2-(2-propenyl)-1,3-propanediol pale yellowliquid

Rf value: 0.55 (chloroform:methanol: 5:1)

¹ H-NMR (CDCl₃ -CD₃ OD) δ(ppm): 1.95 (3H, s), 2.33 (2H, d, J=7.3 Hz),3.49 (2H, d, J=11.7 Hz), 3.64 (2H, d, J=11.7 Hz), 5.07-5.10 (2H, m),5.66-5.90 (1H, m)

IR ν (neat): 3310, 1641 cm⁻¹

MS(EI): 174 (M+1)

EXAMPLE 384 2-Amino-2-(2-propenyl)-1,3-propanediol 8/5 hydratehydrochloride brown liquid

¹ H-NMR (CDCl₃) δ(ppm): 2.33 (2H, d, J=10.7 Hz), 3.56 (4H, dd, J=3.0 Hz,J=19.0 Hz), 3.39 (11H, br.s), 5.14-5.22 (2H, m), 5.62-5.23 (1H, m)

IR ν (neat): 3445, 1614, 1516 cm⁻¹

MS(EI): 132 (M+1)

elemental analysis: calculated C 36.68, H 8.82, N 7.13 found C 36.27, H8.47, N 7.26

EXAMPLE 385 2-Amino-2-phenylmethyloxymethyl-1,3-propanediol 1/10 hydratehydrochloride

melting point=113°-114° C.

EXAMPLE 386 2-Acetamido-1,3-diacetoxy-2-phenylmethyloxymethylpropane

IR ν (neat): 3307, 2934, 1743, 1662, 1549 cm⁻¹

EXAMPLE 387 2-Amino-2- 2-(4-nonylphenyl)ethyl!-1,3-propanediol 1/3hydrate hydrochloride

melting point=95°-97° C.

elemental analysis: calculated C 66.00, H 10.15, N 3.85 found C 66.19, H10.24, N 3.86

EXAMPLE 388 2-Acetamido-1,3-diacetoxy-2- 2-(4-nonylphenyl)ethyl!propane

melting point=95°-98° C.

EXAMPLE 389 2-Acetamido-2- 2-(4-undecylphenyl)ethyl!-1,3-propanediol

melting point=90°-91° C.

EXAMPLE 390 2-Amino-2- 2-(4-undecylphenyl)ethyl!-1,3-propanediol

melting point=105°-107° C.

¹ H-NMR (CDCl₃) δ(ppm): 0.88 (3H, t, J=6.8 Hz), 1.20-1.80 (24H, m), 2.56(2H, t, J=7.8 Hz), 2.61 (2H, m), 3.51 (2H, d, J=10.8 Hz), 3.61 (2H, d,J=10.8 Hz), 7.10 (4H, s)

EXAMPLE 3912-Acetamido-4-(4-heptylphenyl)-2-hydroxymethyl-1,4-butanediol

melting point=117°-118° C.

EXAMPLE 392 2-Acetamido-4-(4-octylphenyl)-2-hydroxymethyl-1,4-butanediol

melting point=118°-119° C.

EXAMPLE 393 2-Acetamido-2- 2-(4-heptylphenyl)ethyl!-1,3-propanediol

melting point=89°-90° C.

EXAMPLE 394 2-Acetamido-2-1,3-propanediyl-2-(4-heptylphenyl)ethyl!ylidene diacetate

melting point=108°-109° C.

EXAMPLE 395 2-Amino-2- 2-(4-heptylphenyl)ethyl!-1,3-propanediolhydrochloride

melting point=134°-135° C.

¹ H-NMR (DMSO only) δ(ppm): 0.83 (3H, t, J=6 Hz), 1.17-2.33 (8H, m),1.45-1.58 (2H, m), 1.69-1.79 (2H, m), 2:48-2.62 (4H, m), 3.34 (2H,br.s), 3.48 (4H, s), 7.08 (4H, s), 7.47 (3H, br.s)

IR ν (KBr)_(max) : 3369, 2926, 1515, 1467, 1059 cm⁻¹

EXAMPLE 396 2-Acetamido-1,3-propanediyl-2-2-(4-tetradecylphenyl)ethyl!ylidene diacetate

melting point=125°-126° C.

EXAMPLE 397 2-Amino-2- 2-(4-tetradecylphenyl)ethyl!-1,3-propanediolhydrochloride

melting point=123°-124° C.

¹ H-NMR (DMSO-CDCl₃) δ(ppm): 0.80 (3H, t, J=6 Hz), 1.02-1.24 (22H, m),1.45-1.53 (2H, m), 1.88 (2H, m, J=4 Hz), 2.46 (2H, t, J=6 Hz), 2.56-2.62(2H, m), 3.56 (2H, dd, J=12 Hz, 31 Hz), 3.57 (2H, dd, J=12 Hz, 31 Hz),4.90 (2H, br.s), 7.01 (4H, dd, J=7 Hz, 12 Hz), 7.99 (3H, br.s)

IR ν (KBr)_(max) : 3374, 3268, 2922, 1516, 1469, 1069 cm⁻¹

EXAMPLE 398 N-Methylamino-2- 2-(4-octylphenyl)ethyl!-1,3-propanediol

¹ H-NMR (CDCl₃) δ(ppm): 0.80 (3H, t, J=7 Hz), 1.09-1.39 (10H, m),1.45-1.56 (2H, m), 1.56-1.76 (2H, m), 2.41 (3H, s), 2.44-2.61 (4H, m),3.32 (3H, br.s), 3.47-3.81 (4H, m), 7.01 (4H, s)

IR ν (neat): 3386, 2927, 1467, 1058, 909 cm⁻¹

EXAMPLE 399 2-Amino-4-(4-heptylphenyl)-2-hydroxymethyl-1,4-butanediolhydrochloride

melting point=105°-108° C.

¹ H-NMR (DMSO) δ(ppm): 0.86 (3H, t, J=7 Hz), 1.17-1.36 (8H, m),1.46-1.63 (2H, m), 1.76 (2H, dd, J=7 Hz, 18 Hz), 2.54 (2H, t, J=7 Hz),3.34 (3H, br.s), 3.58 (4H, dd, J=11 Hz, 35 Hz), 4.83-4.92 (1H, m), 6.99(3H, br.s), 7.18 (4H, dd, J=7 Hz, 37 Hz)

IR ν (KBr)_(max) : 3388, 2928, 1610, 1511, 1063 cm⁻¹

EXAMPLE 400 2-Amino-4-(4-octylphenyl)-2-hydroxymethyl-1,4-butanediol 1/4hydrate

¹ H-NMR (CDCl₃) δ(ppm): 0.86 (3H, t, J=7 Hz), 1.22-1.38 (10H, m),1.54-1.68 (3H, m), 1.68-1.79 (1H, m), 2.59 (2H, t, J=7 Hz), 3.40 (3H,br.s), 3.50 (4H, dd, J=8 Hz, 38 Hz), 3.63 (2H, br.s), 4.91 (1H, m), 7.20(4H, dd, J=6 Hz, 30 Hz)

IR ν (neat): 3340, 3286, 2925, 1465, 1027 cm⁻¹

The action and effect of the present invention are explained in detailby illustrating experimental examples in the following.

For determining the immunosuppressive activity, various immune reactionsusing lymphocytes of mouse, rat or human are usable. It may bedetermined with high sensitivity, for example, by an allogenic mixedlymphocyte reaction (allogenic MLR) of mouse, rat or human.

The allogenic MLR is a blastogenesis of lymphocytes induced by a mixedculture of lymphocytes derived from two kinds of cells which areallogenic but have different major histocompatibility antigens, such asspleen cells, lymph node cells and peripheral blood lymphocytes. Theallogenic MLR is a phenomenon induced by and reflects the difference inmajor histocompatibility antigens of the donors of the lymphocytes, anda blastogenesis phenomenon of the lymphocytes is not developed by amixed culture of the lymphocytes from monozygotic twins. Accordingly,allogenic MLR is widely used for the donor-recipient selection in organtransplantations.

When allogenic MLR is desired, one way-MLR, wherein the lymphocytes ofone of them are used as stimulator cells upon X-ray irradiation ortreatment with mitomycin C to inhibit proliferation and theblastogenesis of the other lymphocytes (responder cells) is determined,may be used.

Further, the immunosuppressive activity may be determined as an activityto inhibit induction of cytotoxic T cells having the majorhistocompatibility antigen restrictive property during allogenic MLR.

Also, the immunosuppressive activity may be determined, besidesallogenic MLR, as an activity to inhibit the blastogenesis of thelymphocytes induced by the stimulation of various mitogens such asconcanavalin A, phytohemaggulutinin and pokeweed mitogen or as anactivity to inhibit the proliferation of the lymphocytes induced by acytokine (e.g. interleukin 1, 2, 3, 4, 5 or 6) having an activity toreinforce the proliferation or promote the differentiation of thelymphocytes such as T cells or B cells, or manifestation of suchfunction. In addition, it is possible to evaluate the immunosuppressiveactivity according to the inhibition of the production of thesecytokines from T cells or macrophages.

Alternatively, the activity may be evaluated as an activity to inhibitinduction of allogenic cells-specific cytotoxic T cells induced inspleen cells of mouse previously immunized with, for example, allogeniccells by intraperitoneally, orally, intravenously, intradermally,subcutaneously or intramuscularly administering a compound to mice; asan activity to inhibit the production of an allogenic cells-specificantibody produced in the blood serum of mouse immunized with allogeniccells or the like; or as an activity to inhibit rejection on organtransplantation between allogenic mice, rats, dogs and so on,graft-versus-host reaction, or delayed type allergy and adjuvantarthritis.

Moreover, the immunosuppressive activity may be evaluated as an activityto inhibit, for example, production of an anti-DNA antibody, productionof a rheumatoid factor, nephritis, abnormal proliferation of lymphocytesor urinary protein; or a macrobiotic effect by the administration of thecompound to MRL/lpr mouse, NZB/WFx mouse, BXSB mouse, NOD mouse and thelike which are model animals with autoimmune diseases.

Experimental Example 1 (inhibition of allogenic mixed lymphocytereaction in mouse)

The mouse allogenic mixed lymphocyte reaction (hereinafter referred toas mouse allogenic MLR) is carried out by a mixed culture of spleencells of BALB/c mouse as responder cells and spleen cells of C57BL/6mouse treated with mitomycin C as stimulator cells at the same ratio.

The reaction cells are prepared as follows. A spleen is removed from a5-6 weeks old BALB/c mouse and a single cell suspension of spleen cellsis obtained by the use of an RPMI1640 medium (containing kanamycinsulfate 60 μg/ml, penicillin G potassium 100 units/ml,N-2-hydroxyethylpiperazine-N'-2-ethanesulfonate 10 mM, 0.1% sodiumhydrogencarbonate and L-glutamine 2 mM) supplemented with 5%heat-inactivated fetal calf serum (hereinafter referred to as FCS).After hemolysis treatment, the suspension is adjusted to a concentrationof 10⁷ cells/ml by the use of an RPMI1640 medium containing 10⁻⁴ M2-mercaptoethanol and 10% FCS and used as a reaction cell suspension.

The stimulator cells are prepared as follows. A spleen is removed from a5-6 weeks old C57BL/6 mouse and a single cell suspension of spleen cellis obtained by the use of an RPMI1640 medium. After hemolysis treatment,the suspension is treated with 40 μg/ml mitomycin C at 37° C. for 60minutes. After washing three times, the suspension is adjusted to aconcentration of 107 cells/ml by the use of an RPMI1640 mediumcontaining 10⁻⁴ M 2-mercaptoethanol and 10% FCS and used as a stimulatorcell suspension.

The responder cell suspension (50 μl) prepared by the method describedabove,-the stimulator cell suspension (50 μl) prepared by the methoddescribed above and a test sample (100 μl) prepared by the use of anRPMI1640 medium containing 10% FCS are placed in a 96 well flat-bottomedmicro testplate and cultured at 37° C. under 5% CO₂ -95% air for 4 days.

The blastogenesis reaction of lymphocytes in mouse allogenic MLR isdetermined by a method using ³ H-thymidine uptake as an index. Namely,after the culture, ³ H-thymidine 18.5 KBq/well is added and the cellsare cultured for 4 hours. The cells are collected by a cell harvesterand the radioactivity incorporated into the cells is determined by aliquid scintillation counter and used as an index for the lymphocyteblastogenesis in mouse allogenic MLR. The inhibition of mouse allogenicMLR is calculated by the formula below and evaluated accordingly.

Of the compounds of the present invention, the preferred show an IC₅₀value (a concentration to inhibit by 50%) of from about 1 nM to about 50nM in a mouse allogenic mixed lymphocyte reaction. ##EQU1## ExperimentalExample 2 Inhibition of proliferation of interleukin 2 (IL-2)-dependentmouse T cell line CTLL-2 induced by IL-2!

An IL-2-dependent mouse T cell line CTLL-2 is prepared to aconcentration of 2×10⁵ cell/ml in an RPMI1640 medium containing 10% FCS.A cell suspension thereof (50 μl), recombinant human IL-2 (rh-IL-2) 40U/ml (50 μl) and a test sample (100 μl) prepared by the use of anRPMI1640 medium containing 10% FCS are placed in a 96 well flat-bottomedmicro testplate and cultured at 37° C. under 5% CO₂ -95% air for 68hours. After the culture, 100 μl of the supernatant of each well isremoved and a 5 mg/ml MTT3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide! solutionis added to each well by 20 μl and the cells are incubated at 37° C. for4 hours. Then, 0.01N hydrochloric acid solution (100 μl) containing 10%sodium dodecyl sulfate is added thereto and the cells are incubated at37° C. overnight. The purple formazan crystals produced are dissolvedand the absorbance at 570 nm is measured using a microplate absorbancephotometer and used as an index of-the proliferation of theIL-2-dependent CTLL-2 cells. The inhibition (%) of the IL-2 dependentproliferation is calculated by the following formula.

Of the compounds of the present invention, the preferred show an IC₅₀value (a concentration to inhibit by 50%) of from about 1 nM to about 50nM in the IL-2-dependent proliferation of mouse T cell line CTLL-2.##EQU2## Experimental Example 3 (take-prolonging effect on allogenicskin graft in rat)

A full-thickness graft (1.5×1.5 cm) of a 4 weeks-old male WKAH rat orLEW rat is grafted to a graft floor on the back of a 4 weeks-old maleF344 rat by suture. The graft is covered with a sterile gauze and bound.The bandage is removed 5 days after the grafting and the skin graft isobserved daily until it is rejected. The skin graft is considered to berejected when 90% or more of the epithelium of the skin graft showednecrosis and turned brown. The number of days from the grafting torejection is taken as a graft taking days. A test compound isintraperitoneally, intravenously or orally administered once a day and10 times from the grafting day to day 9.

When a test compound is not administered, an average taking days forgrafting the skin of a HAH rat to an F344 rat was 6.6±0.5 and that forgrafting the skin of an LEW rat to an F344 rat was 8.2±0.4.

Of the compounds of the present invention, a preferred compound showed,when administered at 0.1-10 mg/kg, an average taking days of not lessthan 10 for grafting the skin of a WKAH rat to an F344 rat and not lessthan 20 for grafting the skin of an LEW rat to an F344 rat, thus showinga take-prolonging effect statistically significant as compared with thegroup without administration of the test compound.

Experimental Example 4 (inhibition of adjuvant arthritis in rat)

Dead tuberculosis bacterium (R35H5v-1 strain, 0.5 mg) was suspended asan adjuvant in 1.0 ml of liquid paraffin and innoculated to the tailhead of a 10 weeks-old male LEW rat to cause adjuvant arthritis. Afterthe innoculation of the adjuvant, the rats are observed daily todetermine the onset of arthritis, ratio of the onset cases and bodyweight changes. At day 21, swelling of the hind limbs and the weight ofthe organs are measured. A test compound is intravenously or orallyadministered from the adjuvant innoculation day once a day and 22 timesup to day 21.

When the test compound was not administered, arthritis was found in all7 rats innoculated with adjuvant at day 9.6±0.5, along with swelling anddestruction of the bone of the hind limbs. Along with the onset of theadjuvant arthritis, decrease in body weight, increase in the weights ofkidney and adrenal and decrease in the thymus weight were found.

Of the compounds of the present invention, a preferred compound delayedthe onset of and decreased the ratio of the onset cases of the adjuvantarthritis to a statistically significant degree and significantlysuppressed swelling and bone destruction of the hind limbs by theadministration of 0.1-10 mg/kg thereof. In addition, decrease in bodyweight, increase in the weights of kidney and adrenal and decrease inthe thymus weight, which accompany onset of adjuvant arthritis, weresignificantly reduced.

As is evident from the various experiments inclusive of pharmacologicalexperiments as noted above, the compounds of the present invention andsalts thereof have superior immunosuppressive action and are useful aspharmaceuticals.

Formulation Examples

    ______________________________________                                        (1) Soft capsules (per capsule)                                               ______________________________________                                        Compound of the invention                                                                         30 mg                                                     Polyethylene glycol 300                                                                          300 mg                                                     Polysolbate 80      20 mg                                                     Total              350 mg                                                     ______________________________________                                    

Production method

Polyethylene glycol 300 and Polysorbate 80 are added to a compound ofthe present invention and the mixture is packed in a soft capsule.

    ______________________________________                                        (2) Injections (per 10 ml in one ampoule)                                     ______________________________________                                        Compound of the invention                                                                       0.3%                                                        Polyethylene glycol 300                                                                        20%                                                          Ethanol          60%                                                          Injectable distilled water                                                                     amount to make the total 10 ml                               ______________________________________                                    

Production method

Ethanol and polyethylene glycol 300 are added to a compound of thepresent invention and injectable distilled water is added to reach thetotal amount.

Injections containing 30ml of the compound of the present invention inone ampoule (10 ml) are thus obtained.

While the present invention has been described in detail by thespecification including examples, the present invention is subject tovarious modifications and changes insofar as they are within the spiritand scope of the present invention.

We claim:
 1. A 2-amino-1,3-propanediol compound of having the formula##STR437## wherein Ra is a straight- or branched chain alkyl having 12to 22 carbon atoms, which may have, in the chain, a bond or a heteroatom selected from the group consisting of a double bond, a triple bond,oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- where R⁶ is hydrogen,alkyl, aralkyl, acyl or alkoxycarbonyl, and carbonyl, and which mayhave, as a substituent, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy,acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl,alkoxycarbonylamino, acyloxy, alkylcarbamoyl, nitro, halogen, amino,hydroxyimino, hydroxy or carboxy, andR² b, R³ b, R⁴ b and R⁵ b are thesame or different and each is a hydrogen, an alkyl or an acyl; or apharmaceutically acceptable salt thereof.
 2. A 2-amino-1,3-propanediolcompound of claim 1, having the formula ##STR438## wherein Rb is astraight- or branched chain alkyl having 13 to 20 carbon atoms, whichmay have, in the chain, an oxygen atom and which may have, as asubstituent, nitro, halogen, amino, hydroxy or carboxy, andR² c and R³ care the same or different and each is a hydrogen or an alkyl, or apharmaceutically acceptable salt thereof.
 3. A 2-amino-1,3-propanediolcompound of claim 1 or 2, having the formula ##STR439## wherein Rc is astraight-or branched chain alkyl having 13 to 20 carbon atoms or astraight- or branched chain alkyl having 13 to 20 carbon atoms which issubstituted by halogen, or a pharmaceutically acceptable salt thereof.4. A 2-amino-1,3-propanediol compound of any one of claims 1 or 2, whichis selected from the group consistingof2-amino-2-tridecyl-1,3-propanediol,2-amino-2-tetradecyl-1,3-propanediol,2-amino-2-pentadecyl-1,3-propanediol,2-amino-2-hexadecyl-1,3-propanediol,2-amino-2-heptadecyl-1,3-propanediol,2-amino-2-octadecyl-1,3-propanediol,2-amino-2-nonadecyl-1,3-propanediol, 2-amino-2-icosyl-1,3-propanediol,2-amino-2-(12-fluorododecyl)-1,3-propanediol and2-amino-2-(14-fluorotetradecyl)-1,3-propanediol, or a pharmaceuticallyacceptable salt thereof.
 5. A 2-amino-1,3-propanediol compound of claim3, which is selected from the group consistingof2-amino-2-tridecyl-1,3-propanediol,2-amino-2-tetradecyl-1,3-propanediol,2-amino-2-pentadecyl-1,3-propanediol,2-amino-2-hexadecyl-1,3-propanediol,2-amino-2-heptadecyl-1,3-propanediol,2-amino-2-octadecyl-1,3-propanediol,2-amino-2-nonadecyl-1,3-propanediol, 2-amino-2-icosyl-1,3-propanediol,2-amino-2-(12-fluorododecyl)-1,3-propanediol and2-amino-2-(14-fluorotetradecyl)-1,3-propanediol, or a pharmaceuticallyacceptable salt thereof.
 6. A method for immunosuppression, whichcomprises administering to a mammal an effective amount of a compound ofclaim
 1. 7. A method for suppression of rejection in organ or bonemarrow transplantation in a mammal, which comprises administering to amammal an effective amount of a compound of claim
 1. 8. A method forprevention and treatment of autoimmune disease, which comprisesadministering to a mammal an effective amount of a compound of claim 1.9. The method according to claim 8, wherein the autoimmune disease isrheumatoid arthritis.
 10. A method for prevention and treatment ofpsoriasis or atopic dermatitis, which comprises administering to amammal an effective amount of a compound of claim
 1. 11. A method forprevention and treatment of bronchial asthma or pollinosis, whichcomprises administering to a mammal an effective amount of a compound ofclaim 1.